Total synthesis of (-)-ratjadone

被引：57

作者：

Williams, DR ^{[1
]}

Ihle, DC ^{[1
]}

Plummer, SV ^{[1
]}

机构：

[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 09期

关键词：

D O I：

10.1021/ol015753k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A convergent asymmetric synthesis of (-)-ratjadone (1) has been achieved, confirming the assignments of stereochemistry for the naturally occurring antifungal metabolite.

引用

页码：1383 / 1386

页数：4

共 53 条

[1] Selective dihydroxylation of non-conjugated dienes in favor of the terminal olefin [J].

Andrus, MB ;

Lepore, SD ;

Sclafani, JA .

TETRAHEDRON LETTERS, 1997, 38 (23) :4043-4046

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[3] The first total synthesis of (+)-ratjadone [J].

Bhatt, U ;

Christmann, M ;

Quitschalle, M ;

Claus, E ;

Kalesse, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1885-1893

[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].

BROWN, HC ;

BHAT, KS ;

RANDAD, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576

[5] A PRACTICAL ROUTE TOWARDS ALPHA,BETA-UNSATURATED DELTA-LACTONES BASED ON A [3+3] STRATEGY - SYNTHESIS OF (-)-ARGENTILACTONE [J].

CARRETERO, JC ;

GHOSEZ, L .

TETRAHEDRON LETTERS, 1988, 29 (17) :2059-2062

[6] The synthesis of the C15-C24 segment of ratjadone [J].

Christmann, M ;

Kalesse, M .

TETRAHEDRON LETTERS, 1999, 40 (40) :7201-7204

[7]

Christmann M, 2000, ANGEW CHEM INT EDIT, V39, P4364, DOI 10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO

[8]

2-G

[9] Vinylogous Mukaiyama aldol reactions with triarylboranes [J].

Christmann, M ;

Kalesse, M .

TETRAHEDRON LETTERS, 2001, 42 (07) :1269-1271

[10] Synthesis of the C6-C16 polyene fragment of ratjadone, a potent cytotoxic metabolite from Sorangium cellulosum [J].

Claus, E ;

Kalesse, M .

TETRAHEDRON LETTERS, 1999, 40 (22) :4157-4160

← 1 2 3 4 5 6 →