References and Notes
1a
Kunze B.
Jansen R.
Hofle G.
Reichenbach H.
J. Antibiot.
1994,
47:
881
1b
Jansen R.
Washausen P.
Kunze B.
Reichenbach H.
Hofle G.
Eur. J. Org. Chem.
1999,
1085
2
Jansen R.
Kunze B.
Reichenbach H.
Hofle G.
Liebigs Ann.
1996,
285
3a
Feutrill JT.
Lilly MJ.
Rizzacasa MA.
Org. Lett.
2000,
2:
3365
3b
Chakraborty TK.
Jayaprakash S.
Tetrahedron Lett.
2001,
42:
497
3c
Dias LC.
de Oleveira LG.
Org. Lett.
2001,
3:
3951
3d
Chakraborty TK.
Jayaprakash S.
Laxman P.
Tetrahedron
2001,
57:
9461
3e
Feutrill JT.
Lilly MJ.
Rizzacasa MA.
Org. Lett.
2002,
4:
525
3f
Chakraborty TK.
Laxman P.
Tetrahedron Lett.
2002,
43:
2645
3g
Crowley PJ.
Aspinall IH.
Gillen K.
Godfrey CRA.
Devillers IM.
Munns GR.
Sageot O.-A.
Swanborough J.
Worthington PA.
Williams J.
Chimia
2003,
57:
685
3h
Dias LC.
Oleveira LG.
Vilcachagua JD.
Florian N.
J. Org. Chem.
2005,
70:
2225
3i
Chakraborty TK.
Laxman P.
Tetrahedron Lett.
2002,
44:
4989
3j
Feutrill JT.
Rizzacasa MA.
Aust. J. Chem.
2003,
56:
783
3k
Gurjar MK.
Khaladkar TP.
Borhade RG.
Murugan A.
Tetrahedron Lett.
2003,
44:
5183
3l
Raghavan S.
Reddy SR.
Tetrahedron Lett.
2004,
45:
5593
See, for example,
4a
Barry CSJ.
Crosby StR.
Harding JR.
Hughes RA.
King CD.
Parker GD.
Willis CL.
Org. Lett.
2003,
5:
2429
4b
Yang X.-F.
Mague JT.
Li C.-J.
J. Org. Chem.
2001,
66:
739
4c
Yadav JS.
Reddy BVS.
Sekhar KC.
Gunasekar D.
Synthesis
2001,
885
4d
Yadav JS.
Reddy BVS.
Reddy MS.
Niranjan N.
J. Mol. Catal. A: Chem.
2004,
210:
99
4e
Yadav JS.
Reddy BVS.
Reddy MS.
Niranjan N.
Prasad AR.
Eur. J. Org. Chem.
2003,
1779
5a
Aubele DL.
Wan S.
Floreancig PE.
Angew. Chem. Int. Ed.
2005,
44:
3485
5b
Barry CS.
Bushby N.
Harding JR.
Willis CS.
Org. Lett.
2005,
7:
2683
5c
Cossey KN.
Funk RL.
J. Am. Chem. Soc.
2004,
126:
12216
5d
Crosby SR.
Harding JR.
King CD.
Parker GD.
Willis CL.
Org. Lett.
2002,
4:
3407
5e
Marumoto S.
Jaber JJ.
Vitale JP.
Rychnovsky SD.
Org. Lett.
2002,
4:
3919
5f
Kozmin SA.
Org. Lett.
2001,
3:
755
5g
Jaber JJ.
Mitsui K.
Rychnovsky SD.
J. Org. Chem.
2001,
66:
4679
5h
Kopecky DJ.
Rychnovsky SD.
J. Am. Chem. Soc.
2001,
123:
8420
5i
Rychnovsky SD.
Thomas CR.
Org. Lett.
2000,
2:
1217
5j
Rychnovsky SD.
Yang G.
Hu Y.
Khire UR.
J. Org. Chem.
1997,
62:
3022
5k
Su Q.
Panek JS.
J. Am. Chem. Soc.
2004,
126:
2425
6a
Yadav JS.
Reddy MS.
Prasad AR.
Tetrahedron Lett.
2005,
46:
2133
6b
Yadav JS.
Reddy MS.
Rao PP.
Prasad AR.
Tetrahedron Lett.
2006,
47:
4397
6c
Yadav JS.
Reddy MS.
Prasad AR.
Tetrahedron Lett.
2006,
47:
4937
6d
Yadav JS.
Reddy MS.
Prasad AR.
Tetrahedron Lett.
2006,
47:
4995
7
Furrow ME.
Schaus SE.
Jacobsen EN.
J. Org. Chem.
1998,
68:
6776
8a
Trost BM.
Kondo Y.
Tetrahedron Lett.
1991,
32:
1613
8b
Walsh TF.
Toupence RB.
Ujjainwalla F.
Young JR.
Goulet MT.
Tetrahedron
2001,
57:
5233
9
Fuwa H.
Okamura Y.
Natsugari H.
Tetrahedron
2004,
60:
5341
10a
Quinn KJ.
Isaacs AK.
Christopher BAD.
Szklarz SC.
Arvary RA.
Org. Lett.
2005,
7:
1243
10b
Connon SJ.
Blechert S.
Angew. Chem. Int. Ed.
2000,
42:
1900
11a
Whitcombe NJ.
Hii KK.
Gibson SE.
Tetrahedron
2001,
57:
7449
11b
Crisp GT.
Chem. Soc. Rev.
1998,
27:
427
11c
Beletskaya IP.
Cheprakov AV.
Chem. Rev.
2000,
100:
3009
12 Selected Physical Data. Compound 9: clear oil; R
f
= 0.5 (EtOAc-hexane, 1:9). IR (KBr): νmax = 2828, 2856, 1643, 1458, 1092, 838, 697 cm-1. 1H NMR (300 MHz, CDCl3): δ = 7.37-7.17 (m, 5 H), 4.47 (d, 1 H, J = 12.0 Hz), 4.42 (d, 1 H, J = 12.0 Hz), 3.57 (dd, 1 H, J = 10.5, 5.2 Hz), 3.50-3.42 (m, 2 H), 3.33-3.23 (m, 5 H), 3.16 (dd, 1 H, J = 9.8, 1.5 Hz), 2.87 (dt, 1 H, J = 10.5, 4.5 Hz), 2.14-1.98 (m, 2 H), 1.50-1.38 (m, 1 H), 1.10-1.02 (m, 1 H), 0.88 (d, 3 H, J = 6.4 Hz), 0.84 (s, 9 H), 0.81 (d, 3 H, J = 6.7 Hz), 0.03 (s, 6 H). 13C NMR (75 MHz, CDCl3): δ = 138.8, 128.2, 127.4, 127.3, 82.5, 79.9, 75.9, 73.5, 72.9, 66.4, 56.0, 38.4, 34.2, 33.0, 25.8, 18.2, 12.1, 9.6, -5.2, -5.3. LSI-MS: m/z = 445 [M+ + Na], 423 [M+ + H].
Compound 13: white solid; mp 158-160 °C; R
f
= 0.6 (EtOAc-hexane, 1:9). IR (KBr): νmax = 2969, 2928, 2880, 1678, 1433, 1099, 712 cm-1. 1H NMR (300 MHz, CDCl3): δ = 4.60-4.54 (m, 3 H), 3.72 (dd, 1 H, J = 10.1, 3.1 Hz), 3.57 (t, 1 H, J = 8.5 Hz), 3.44 (dt, 1 H, J = 8.5, 2.3 Hz), 3.40-3.29 (m, 4 H), 3.28 (s, 3 H), 2.12-2.02 (m, 1 H), 1.80-1.68 (m, 1 H), 1.72 (s, 3 H), 0.94 (d, 3 H, J = 7.0 Hz), 0.90 (d, 3 H, J = 7.0 Hz). 13C NMR (75 MHz, CDCl3): δ = 153.2, 96.4, 95.9, 78.9, 78.3, 70.0, 55.1, 54.9, 33.8, 33.7, 19.6, 13.7, 9.5. LSI-MS: m/z = 267 [M+ + Na].
Compound 5: clear oil; R
f
= 0.3 (EtOAc-hexane, 1:3); [α]D
20 -3.8 (c 1.80, CH2Cl2); IR (film): ν max = 3453, 2970, 2931, 2827, 1599, 1454, 1374, 1191, 1090, 971 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.40 (d, 2 H, J = 7.6 Hz), 7.32 (t, 2 H, J = 6.8 Hz), 7.24 (tt, 1 H, J = 1.5, 7.6 Hz), 6.59 (d, 1 H, J = 16.0 Hz), 6.21 (dd, 1 H, J = 7.6, 16.0 Hz), 4.07 (dd, 1 H, J = 1.5, 7.6 Hz), 3.82 (dd, 1 H, J = 3.8, 11.4 Hz), 3.56 (dd, 1 H, J = 11.4, 4.5 Hz), 3.52 (s, 3 H), 3.31 (s, 3 H), 3.29 (dd, 1 H, J = 3.0, 9.9 Hz), 3.01 (br s, 1 H), 1.90-1.85 (m, 2 H), 1.20 (d, 3 H, J = 6.8 Hz), 0.91 (d, 3 H, J = 6.8 Hz). 13C NMR (75 MHz, CDCl3): δ = 136.7, 132.1, 129.2, 128.6, 127.6, 126.4, 88.2, 81.1, 64.3, 61.5, 56.3, 42.2, 35.8, 16.1, 10.3. ESI-HRMS: m/z calcd for C17H26O3Na [M + Na+]: 301.1779; found: 301.1791.
Compound 18: light yellowish oil; R
f
= 0.5 (EtOAc-hexane, 1:9); [α]D
20 -6.7 (c 0.2 CHCl3) {Lit.
[3d]
[α]D
20 -7.91 (c 0.2 CHCl3)}. IR (film): νmax = 2974, 2929, 1710, 1609, 1450, 1367, 1238, 1154, 1092, 1042, 972 cm-1. 1H NMR (300 MHz, CDCl3): δ = 7.33 (d, 2 H, J = 7.5 Hz) 7.25 (t, 2 H, J = 7.5 Hz), 7.20 (tt, 1 H, J = 8.3, 1.5 Hz), 6.55 (d, 1 H, J = 15.8), 6.10 (m, 2 H), 6.05 (d, 1 H, J = 15.8 Hz), 5.63 (s, 1 H), 4.09 (q, 2 H, J = 6.7 Hz), 4.03 (m, 1 H), 3.51 (s, 3 H), 3.29 (s, 3 H), 3.13 (dd, 1 H, J = 9.8, 2.2 Hz), 2.50 (m, 2 H), 2.26 (d, 3 H, J = 1.5 Hz), 1.50 (m, 1 H) 1.26 (t, 2 H, J = 7.5 Hz), 1.19 (d, 3 H, J = 6.7 Hz), 0.82 (d, 3 H, J = 6.7 Hz). 13C NMR (50 MHz, CDCl3): δ = 167.2, 152.5, 140.0, 136.7, 133.9, 132.0, 129.1, 128.5, 127.5, 126.3, 118.0, 86.3, 81.0, 61.4, 59.5, 56.4, 42.6, 40.0, 18.7, 14.3, 13.9, 9.6. ESI-HRMS: m/z calcd for C24H34O4Na [M + Na+]: 409.2354; found: 409.2356.
13 Sulfone 17 was prepared from mercaptobenzothiazole in three steps in 62% overall yield as shown in Scheme 3.