Total synthesis of (+)-spongistatin 1. An effective second-generation construction of an advanced EF Wittig salt, fragment union, and final elaboration

被引：57

作者：

Smith, AB ^{[1
]}

Zhu, WY

Shirakami, S

Sfouggatakis, C

Doughty, VA

Bennett, CS

Sakamoto, Y

机构：

[1] Univ Penn, Dept Chem, Monell Chem Senses Ctr, Philadelphia, PA 19104 USA

[2] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 05期

关键词：

D O I：

10.1021/ol034037a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A stereocontrolled, total synthesis of (+)-spongistatin 1 (1) has been achieved. Union of a second-generation EF Wittig salt (+)-3 with the advanced ABCD aldehyde (-)-4, followed by regioselective macrolactonization and global deprotection afforded (+)-spongistatin 1 (1). The longest linear sequence, 29 steps, proceeded in 0.5% overall yield.

引用

页码：761 / 764

页数：4

共 36 条

[1] CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE [J].

BROWN, HC ;

BHAT, KS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5919-5923

[2] Asymmetric total synthesis of spongistatins 1 and 2 [J].

Crimmins, MT ;

Katz, JD ;

Washburn, DG ;

Allwein, SP ;

McAtee, LF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) :5661-5663

[3] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].

CRISPINO, GA ;

JEONG, KS ;

KOLB, HC ;

WANG, ZM ;

XU, DQ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786

[4] Enantioselective total synthesis of altohyrtin C (spongistatin 2) [J].

Evans, DA ;

Trotter, BW ;

Coleman, PJ ;

Côté, B ;

Dias, LC ;

Rajapakse, HA ;

Tyler, AN .

TETRAHEDRON, 1999, 55 (29) :8671-8726

[5] Enantioselective synthesis of altohyrtin C (spongistatin 2):: Fragment assembly and revision of the spongistatin 2 stereochemical assignment [J].

Evans, DA ;

Trotter, BW ;

Côté, B ;

Coleman, PJ ;

Dias, LC ;

Tyler, AN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2744-2747

[6] Enantioselective synthesis of altohyrtin C (spongistatin 2):: Synthesis of the EF-bis(pyran) subunit [J].

Evans, DA ;

Trotter, BW ;

Côté, B ;

Coleman, PJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2741-2744

[7] Enantioselective synthesis of altohyrtin C (spongistatin 2): Synthesis of the AB- and CD-spiroketal subunits [J].

Evans, DA ;

Coleman, PJ ;

Dias, LC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2738-2741

[8]

FUJITA E, 1978, CHEM PHARM BULL, V26, P3743

[9] BIOACTIVE MARINE METABOLITES .48. CINACHYROLIDE-A - A POTENT CYTOTOXIC MACROLIDE POSSESSING 2 SPIRO KETALS FROM MARINE SPONGE CINACHYRA SP [J].

FUSETANI, N ;

SHIMODA, K ;

MATSUNAGA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3977-3981

[10]

Guo JS, 1998, ANGEW CHEM INT EDIT, V37, P187, DOI 10.1002/(SICI)1521-3773(19980202)37:1/2<187::AID-ANIE187>3.0.CO

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