Abstract
An efficient and practical strategy has been developed for the
construction of the antipode of 3,4-dihydroxy-2,5-disubstituted
tetrahydrofuran, goniothalesdiol, isolated from the bark of the Malaysian
tree. The synthetic process is based on the convenient manipulation
via Lewis acid-induced deoxygenation of the highly functionalized
lactone derived from d-glucuronolactone.
Key words
goniothalesdiol - tetrasubstituted tetrahydrofuran - stereoselective deoxygenation - trisubstituted γ-lactone -
d-glucuronolactone
References
1a
Zeng L.
Ye Q.
Oberlies NH.
Shi G.
Gu Z.-M.
He K.
McLaughlin JL.
Nat. Prod. Rep.
1996,
13:
275
1b
Cavé A.
Figadère B.
Laurens A.
Cortes D. In
Progress in the Chemistry of Organic Natural
Products
Vol. 70:
Herz W.
Springer-Verlag;
Wien,
New York:
1997.
p.81
2a
Bauer I.
Maranda L.
Young KA.
Shimizu Y.
Huang S.
Tetrahedron Lett.
1995,
36:
7093
2b
Sakai R.
Rinehart KL.
J. Nat. Prod.
1995,
58:
773
2c
Wipf P.
Lim S.
J. Am. Chem. Soc.
1995,
117:
558
3a
Matsuo Y.
Suzuki M.
Masuda M.
Chem. Lett.
1995,
1043
3b
Morte M.
Tetrahedron
Lett.
1997,
38:
3137
3c
Koert U.
Angew.
Chem., Int. Ed. Engl.
1995,
34:
298
4
Faulkner DJ.
Nat.
Prod. Rep.
1997,
14:
259
5
Seki T.
Satake M.
Mackenzie L.
Kaspar HF.
Yasumoto T.
Tetrahedron
Lett.
1995,
36:
7093
6a
Boukouvalas J.
Fortier G.
Radu I.-I.
J. Org. Chem.
1998,
63:
916
6b
Fernández
de la Pradilla R.
Montero C.
Priego J.
Martínez-Cruz LA.
J. Org. Chem.
1998,
63:
9612
6c
Capon RJ.
Barrow RA.
Skene C.
Rochfort S.
Tetrahedron
Lett.
1997,
38:
7609
6d
Capon RJ.
Barrow RA.
J.
Org. Chem.
1998,
63:
75
6e
Capon RJ.
Barrow RA.
Rochfort S.
Jobling M.
Skene C.
Lacey E.
Gill JH.
Friedel T.
Wadsworth D.
Tetrahedron
1998,
54:
2227
6f
Wang Z.-M.
Shen M.
J. Org. Chem.
1998,
63:
1414
6g
Mori Y.
Sawada T.
Furukawa H.
Tetrahedron Lett.
1999,
40:
731 ; and references cited therein
7a
Stevens DR.
Whiting DA.
J. Chem. Soc., Perkin Trans. 1
1992,
633
7b
Mitra J.
Mitra AK.
J. Chem. Soc., Perkin
Trans. 1
1992,
1285
7c
Maiti G.
Adhikari S.
Roy SC.
J.
Chem. Soc., Perkin Trans. 1
1995,
927
7d
Yoshida S.-I.
Ogiku T.
Ohmizu H.
Iwasaki T.
J. Org. Chem.
1997,
62:
1310
7e
Chen I.-S.
Chen J.-J.
Duh C.-Y.
Tsai I.-L.
Phytochemistry
1997,
45:
991
8a
Yoda H.
Kimura K.
Takabe K.
Synlett
2001,
400
8b
Yoda H.
Maruyama K.
Takabe K.
Tetrahedron: Asymmetry
2001,
12:
1403
8c
Yoda H.
Mizutani M.
Takabe K.
Tetrahedron
Lett.
1999,
40:
4701
9
Cao S.-G.
Wu X.-H.
Sim K.-Y.
Tan BKT.
Pereira JT.
Goh S.-H.
Tetrahedron
1998,
54:
2143
10a
Geran RI.
Greenberg NH.
MacDonald MM.
Schumacher AM.
Abbott BJ.
Cancer
Chemother. Rep.
1972,
3:
1
10b
Talapatra SK.
Basu D.
Deb T.
Goswani S.
Talapatra B.
Indian
J. Chem., Sect. B
1985,
24:
29
10c
Mukai C.
Hirai S.
Hanaoka M.
J.
Org. Chem.
1997,
62:
6619
10d
Tsubuki M.
Kanai K.
Nagase H.
Honda T.
Tetrahedron
1999,
55:
2493 ; and references cited therein
11
Yoda H.
Shimojo T.
Takabe K.
Synlett
1999,
1969
12a
Yoda H.
Mizutani M.
Takabe K.
Heterocycles
1998,
48:
479
12b
Yoda H.
Mizutani M.
Takabe K.
Synlett
1998,
855
13a
Lewis MD.
Cha JK.
Kishi Y.
J. Am. Chem. Soc.
1982,
104:
4976
13b
Kraus GA.
Molina MT.
Walling JA.
J. Org. Chem.
1987,
52:
1273
13c
Yoda H.
Yamazaki H.
Kawauchi M.
Takabe K.
Tetrahedron: Asymmetry
1995,
6:
2669 ; and references cited therein
14 The absolute S-configuration
of the new asymmetric center in 5a was
proved by the transformation into the meso compound 12 through
sequential seven steps as shown below (Figure
[2]
).
15 Coupling reaction of this diol intermediate 13 with Horner-Emmons reagent
interestingly brought about the tricyclic compound 15 directly
in 75% isolated yield as a sole product. It is reasonable
to assume that the formation of 15 would
be resulted in the reaction through intramolecular Michael addition
followed by cyclization of α,β-unsaturated ester 14 (Figure
[3]
).
16 Hydrogenation and simultaneous removal
of the benzyl groups in 9 with Pd on carbon
(10%) under H2 atmosphere were proved to give
a complex mixture. In addition, the hydrogenated final enantiomer
of 1 was unstable and decomposed on standing.
