Subscribe to RSS
DOI: 10.1055/s-2008-1032101
Synthetic Studies toward the Total Synthesis of Amphidinolide H1
Publication History
Publication Date:
26 February 2008 (online)
Abstract
A convergent synthesis of the macrolide core as the immediate precursor to amphidinolide H1 is described, which features a palladium-catalyzed Stille cross-coupling, a methyl ketone diastereoselective aldol reaction, a Mitsunobu esterification, and an intramolecular ring-closing metathesis (RCM) reaction to construct the 26-membered macrocycle as key steps.
Key words
amphidinolide H1 - macrolide - aldol reaction - RCM reaction - Mitsunobu reaction
- 1
Kobayashi J.Ishibashi M.Nakamura H.Ohizumi Y. Tetrahedron Lett. 1986, 27: 5755 - Reviews:
-
2a
Ishibashi M.Kobayashi J. Heterocycles 1997, 44: 543 -
2b
Kobayashi J.Ishibashi M. In Comprehensive Natural Products Chemistry Vol. 8:Mori K. Elsevier; New York: 1999. p.619-649 -
2c
Chakraborty TK.Das S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1: 131 -
2d
Kobayashi J.Tsuda M. Nat. Prod. Rep. 2004, 21: 77 -
2e
Kobayashi J.Kubota T. J. Nat. Prod. 2007, 70: 451 - For total syntheses of amphidinolides families, see:
-
3a
Williams DR.Kissel WS. J. Am. Chem. Soc. 1998, 120: 11198 -
3b
Williams DR.Myers BJ.Mi L. Org. Lett. 2000, 2: 945 -
3c
Williams DR.Meyer KG. J. Am. Chem. Soc. 2001, 123: 765 -
3d
Lam HW.Pattenden G. Angew. Chem. Int. Ed. 2002, 41: 508 -
3e
Maleczka RE.Terrell LR.Geng F.Ward JS. Org. Lett. 2002, 4: 2841 -
3f
Trost BM.Chisholm JD.Wrobleski ST.Jung M. J. Am. Chem. Soc. 2002, 124: 12420 -
3g
Fürstner A.Aïssa C.Riveiros R.Ragot J. Angew. Chem. Int. Ed. 2002, 41: 4763 -
3h
Ghosh AK.Liu C. J. Am. Chem. Soc. 2003, 125: 2374 -
3i
Aïssa C.Riveiros R.Ragot J.Fürstner A. J. Am. Chem. Soc. 2003, 125: 15512 -
3j
Lepage O.Kattnig E.Fürstner A. J. Am. Chem. Soc. 2004, 126: 15970 -
3k
Ghosh AK.Gong G. J. Am. Chem. Soc. 2004, 126: 3704 -
3l
Trost BM.Harrington PE. J. Am. Chem. Soc. 2004, 126: 5028 -
3m
Trost BM.Papillon JPN. J. Am. Chem. Soc. 2004, 126: 13618 -
3n
Colby EA.O’Brien KC.Jamison TF. J. Am. Chem. Soc. 2004, 126: 998 -
3o
Colby EA.O’Brien KC.Jamison TF. J. Am. Chem. Soc. 2005, 127: 4297 -
3p
Trost BM.Harrington PE.Chisholm JD.Wrobleski ST. J. Am. Chem. Soc. 2005, 127: 13589 -
3q
Trost BM.Harrington PE.Chisholm JD.Wrobleski ST. J. Am. Chem. Soc. 2005, 127: 13598 -
3r
Trost BM.Papillon JPN.Nussbaumer T. J. Am. Chem. Soc. 2005, 127: 17921 -
3s
Fürstner A.Kattnig E.Lepage O. J. Am. Chem. Soc. 2006, 128: 9194 -
3t
Fürstner A.Larionov O.Flügge S. Angew. Chem. Int. Ed. 2007, 46: 5545 -
3u
Va P.Roush WR. J. Am. Chem. Soc. 2006, 128: 15960 -
3v
Kim CH.An HJ.Shin WK.Yu W.Woo SK.Jung SK.Lee E. Angew. Chem. Int. Ed. 2006, 45: 8019 -
3w
Nicolaou KC.Brenzovich WE.Bulger PG.Francis TM. Org. Biomol. Chem. 2006, 4: 2119 -
3x
Nicolaou KC.Bulger PG.Brenzovich WE. Org. Biomol. Chem. 2006, 4: 2158 -
3y
Jin J.Chen Y.Li Y.Wu J.Dai WM. Org. Lett. 2007, 9: 2585 -
3z
Colby EA.Jamison TF. Org. Biomol. Chem. 2005, 3: 2675 -
4a
Deng LS.Huang XP.Zhao G. J. Org. Chem. 2006, 71: 4625 -
4b
Fürstner A.Bouchez LC.Funel J.-A.Liepins V.Porée F.-H.Gilmour R.Beaufils F.Laurich D.Tamiya M. Angew. Chem. Int. Ed. 2007, 46: 9265 -
5a
Kobayashi J.Shigemori H.Ishibashi M.Yamasu T.Hirota H.Sasaki T. J. Org. Chem. 1991, 56: 5221 -
5b
Kobayashi J.Shimbo K.Sato M.Shiro M.Tsuda M. Org. Lett. 2000, 2: 2805 - 6
Kobayashi J.Shimbo K.Sato M.Tsuda M. J. Org. Chem. 2002, 67: 6585 - Amphidinolide H and G:
-
7a
Chakraborty TK.Suresh VR. Tetrahedron Lett. 1998, 39: 7775 -
7b
Chakraborty TK.Suresh VR. Tetrahedron Lett. 1998, 39: 9109 -
7c
Sato M.Shimbo K.Tsuda M.Kobayashi J. Tetrahedron Lett. 2000, 41: 503 -
7d
Liesener FP.Kalesse M. Synlett 2005, 2236 -
7e
Liesener FP.Jannsen U.Kalesse M. Synthesis 2006, 2590 -
7f
Petri AF.Schneekloth JS.Mandal AK.Crews CM. Org. Lett. 2007, 9: 3001 -
7g
Deng LS.Ma ZX.Zhang YZ.Zhao G. Synlett 2007, 87 - Structurally related amphidinolides B:
-
8a
Gopalarathnam A.Nelson SG. Org. Lett. 2006, 8: 7 -
8b
Mandal AK.Schneekloth JS.Kuramochi K.Crews CM. Org. Lett. 2006, 8: 427 -
8c
Mandal AK.Schneekloth JS.Kuramochi K.Crews CM. Org. Lett. 2005, 7: 3645 -
8d
Zhang W.Carter RG. Org. Lett. 2005, 7: 4209 -
8e
Zhang W.Carter RG.Yokochi AFT. J. Org. Chem. 2004, 69: 2569 -
8f
Mandal AK.Schneekloth JS.Crews CM. Org. Lett. 2004, 6: 3645 -
8g
Cid MB.Pattenden G. Tetrahedron Lett. 2000, 41: 7373 -
8h
Lee D.-H.Rho M.-D. Tetrahedron Lett. 2000, 41: 2573 -
8i
Chakraborty TK.Thippeswamy D. Synlett 1999, 150 -
8j
Eng HM.Myles DC. Tetrahedron Lett. 1999, 40: 2279 -
8k
Ishiyama H.Takemura T.Tsuda M.Kobayashi J. J. Chem. Soc., Perkin Trans. 1 1999, 1163 -
8l
Ishiyama H.Takemura T.Tsuda M.Kobayashi J. Tetrahedron 1999, 55: 4583 -
8m
Ohi K.Nishiyama S. Synlett 1999, 573 -
8n
Ohi K.Nishiyama S. Synlett 1999, 571 -
8o
Cid MB.Pattenden G. Synlett 1998, 540 -
8p
Ohi K.Shima K.Hamada K.Saito Y.Yamada N.Ohba S.Nishiyama S. Bull. Chem. Soc. Jpn. 1998, 71: 2433 -
8q
Chakraborty TK.Thippeswamy D.Suresh VR.Jayaprakash S. Chem. Lett. 1997, 563 -
8r
Chakraborty TK.Suresh VR. Chem. Lett. 1997, 565 -
8s
Lee D.-H.Lee S.-W. Tetrahedron Lett. 1997, 38: 7909 - 9
White JD.Kawasaki M. J. Org. Chem. 1992, 57: 5292 -
10a
Dess DB.Martin JC. J. Org. Chem. 1983, 48: 4155 -
10b
Corey EJ.Fuchs PL. Tetrahedron Lett. 1972, 13: 3769 -
11a
Yoshida Y.Negishi E. J. Am. Chem. Soc. 1981, 103: 4985 -
11b
Wipf P.Lim S. Angew. Chem., Int. Ed. Engl. 1993, 32: 1095 - 12
Evans DA.Kim AS.Metternich R.Novack VJ. J. Am. Chem. Soc. 1998, 120: 5921 - 13
Gao Y.Klunder JM.Hanson RM.Masamune H.Ko SY.Sharpless KB. J. Am. Chem. Soc. 1987, 109: 5765 -
14a
Milstein D.Stille JK. J. Am. Chem. Soc. 1978, 100: 3636 -
14b
Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508 - 15
Domínguez B.Iglesias B.de Lera AR. Tetrahedron 1999, 55: 15071 -
17a
Mitsunobu O.Yamada M. Bull. Chem. Soc. Jpn. 1967, 40: 2380 -
17b
Mitsunobu O. Synthesis 1981, 1 - 18
Niwa H.Miyachi Y.Okamoto O.Uosaki Y.Kuroda A.Ishiwata H.Yamada K. Tetrahedron 1992, 48: 393 -
20a
Scholl M.Ding S.Lee CW.Grubbs RH. Org. Lett. 1999, 1: 953 -
20b
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4490 - 22
Giudicelli MB.Pieq D.Veyron B. Tetrahedron Lett. 1990, 31: 6527
References and Notes
Aldehyde 4: [α]D 24 -4.0 (c 0.60, CHCl3). IR (film): 2958, 2925, 1726, 1459, 1378, 1026 cm-1. 1H NMR (300 MHz, CDCl3): δ = 5.60-5.40 (m, 3 H), 5.27-5.24 (m, 1 H), 4.96 (s, 1 H), 4.81 (s, 1 H), 3.51 (t, J = 7.5 Hz, 2 H), 3.05 (dd, J = 1.8, 6.9 Hz, 1 H), 2.84-2.80 (m, 1 H), 2.32-2.25 (m, 1 H), 2.12 (dd, J = 6.6, 6.9 Hz, 1 H), 1.94 (dd, J = 5.1, 7.8 Hz, 1 H), 1.97-2.04 (m, 1 H), 1.91 (s, 3 H), 1.90-1.40 (m, 4 H), 1.02 (d, J = 6.6 Hz, 3 H), 0.91 (d, J = 6.6 Hz, 3 H), 0.89 (s, 9 H), -0.33 (s, 6 H). 13C NMR (75 MHz, CDCl3): δ = 202.4, 143.9, 140.8, 135.8, 125.9, 119.0, 115.1, 59.3, 59.2, 48.9, 45.8, 38.9, 37.8, 29.6, 19.6, 19.5, 15.0. MS (EI): m/z calcd for C17H26O2 [M]+: 262; found: 262. HRMS (EI): m/z calcd for C17H26O2 + [M]+: 262.1933; found: 262.1925.
19The stereochemistry of at C18 was confirmed on basis of Mosher ester analysis.
21Diol 2: [α]D 24 -2.2 (c 0.51, CHCl3). IR (neat): 3488, 2925, 1708, 1456, 1263, 1151, 1028 cm-1. 1H NMR (500 Hz, CDCl3): δ = 6.76 (t, J = 6.9 Hz, 1 H), 5.87 (dt, J = 6.8, 15.3 Hz, 1 H), 5.56 (s, 1 H), 5.23 (dd, J = 6.9, 14.6 Hz, 1 H), 5.04 (ddd, J = 3.2, 6.0, 12.6 Hz, 1 H), 4.97 (s, 1 H), 4.81 (s, 1 H), 4.74-4.60 (m, 4 H), 4.19 (d, J = 5.2 Hz, 1 H), 4.05-3.96 (m, 1 H), 3.76 (m, 1 H), 3.70 (m, 1 H), 3.65 (m, 1 H), 3.35 (s, 6 H), 3.09 (br s, 1 H), 3.02 (dd, J = 2.1, 7.9 Hz, 1 H), 2.85 (dt, J = 2.1, 8.6 Hz, 1 H), 2.76-2.63 (m, 2 H), 2.33-2.22 (m, 5 H), 2.16 (m, 1 H), 2.10 (dd, J = 5.1, 7.8 Hz, 1 H), 1.97-1.91 (m, 2 H), 1.83 (s, 3 H), 1.82 (m, 1 H), 1.74 (s, 3 H), 1.71-1.65 (m, 1 H), 1.61-1.49 (m, 2 H), 1.43-1.36 (m, 1 H), 1.29-1.21 (m, 2 H), 1.06 (d, J = 6.6 Hz, 3 H), 1.01 (d, J = 6.8 Hz, 3 H), 0.89 (d, J = 6.6 Hz, 3 H). 13C NMR (125 MHz, CDCl3): δ = 210.0, 168.4, 144.3, 142.5, 141.7, 134.2, 129.3, 128.3, 125.4, 114.7, 97.7, 97.3, 84.0, 81.2, 74.0, 66.0, 65.8, 59.1, 58.9, 56.4, 56.2, 46.8, 46.0, 41.5, 40.1, 39.2, 34.7, 31.8, 30.9, 29.8, 27.7, 19.9, 19.8, 14.7, 14.4, 12.6. ESI-MS: m/z calcd for C36H58O10: 650; found C26H58O10Na+: 673 [M + Na]+. ESI-HRMS: m/z calcd for C36H58O10Na+ [M + Na]+: 673.3922; found: 673.3909.
23When we were preparing this manuscript and trying to deprotect the MOM group, Füstner group reported the first example of total synthesis of the amphidinolide H1 (1), see ref. 4b.