Total synthesis, structural revision, and absolute configuration of (+)-clavosolide A

被引：43

作者：

Son, JB ^{[1
]}

Kim, SN ^{[1
]}

Kim, NY ^{[1
]}

Lee, DH ^{[1
]}

机构：

[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 04期

关键词：

D O I：

10.1021/ol052851n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective synthesis of 3, a revised structure for clavosolide A, was completed. Both H-1 and C-13 NMR spectra of the natural and synthetic compounds were identical, and optical rotation measurements identified the absolute configuration of the natural clavosolide A as the enantiomer of 3.

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页码：661 / 664

页数：4

相关论文

共 31 条

[1]

AKIYAMA S, 1973, TETRAHEDRON LETT, P4115

[2] Total synthesis of a diastereomer of the marine natural product clavosolide A [J].

Barry, CS ;

Bushby, N ;

Charmant, JPH ;

Elsworth, JD ;

Harding, JR ;

Willis, CL .

CHEMICAL COMMUNICATIONS, 2005, (40) :5097-5099

[3] Synthesis of the C1-C21 (C1′-C21′) fragment of the dimeric polyketide natural product SCH 351448 [J].

Bhattacharjee, A ;

Soltani, O ;

De Brabander, JK .

ORGANIC LETTERS, 2002, 4 (04) :481-484

[4] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[5] ASYMMETRIC METHALLYLBORATION OF PROCHIRAL ALDEHYDES WITH METHALLYLDIISOPINOCAMPHEYLBORANE - SYNTHESIS OF 2-METHYL-1-ALKEN-4-OLS IN GREATER-THAN 90-PERCENT ENANTIOMERIC PURITIES [J].

BROWN, HC ;

JADHAV, PK ;

PERUMAL, PT .

TETRAHEDRON LETTERS, 1984, 25 (45) :5111-5114

[6] Formal total synthesis of (+)-methynolide [J].

Cossy, J ;

Bauer, D ;

Bellosta, V .

TETRAHEDRON, 2002, 58 (29) :5909-5922

[7] A simple asymmetric synthesis of cis-2,6-disubstituted tetrahydropyran acetic acid derivatives [J].

Edmunds, AJF ;

Trueb, W .

TETRAHEDRON LETTERS, 1997, 38 (06) :1009-1012

[8] New dimeric macrolide glycosides from the marine sponge Myriastra clavosa [J].

Erickson, KL ;

Gustafson, KR ;

Pannell, LK ;

Beutler, JA ;

Boyd, MR .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (09) :1303-1306

[9] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[10] 1,5-asymmetric induction in boron-mediated β-alkoxy methyl ketone aldol addition reactions [J].

Evans, DA ;

Côté, B ;

Coleman, PJ ;

Connell, BT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10893-10898

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