Biomimetic synthesis of petuniasterone D via the epoxy ester-ortho ester rearrangement

被引：20

作者：

Faraldos, JA ^{[1
]}

Giner, JL ^{[1
]}

机构：

[1] SUNY Coll Environm Sci & Forestry, Dept Chem, Syracuse, NY 13210 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 14期

关键词：

D O I：

10.1021/jo020068s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The side chain of the insecticidal steroid petuniasterone D was synthesized by the biomimetic acid-catalyzed epoxy ester-ortho ester rearrangement. In addition to the natural (22,R,24R)-configuration of the side chain ortho ester, compounds bearing the epimeric (22R,24S)-, (22S,24R)-, and (22S, 24S)- [3.2.1]-bicyclic ortho esters were also produced by stereospecific rearrangement of the corresponding isomeric epoxy esters. Functionalization of the steroid nucleus of the (22R,24R)ortho ester completed the synthesis of the natural product.

引用

页码：4659 / 4666

页数：8

共 35 条

[1] AMANN A, 1987, SYNTHESIS-STUTTGART, P696
[2] BESL H, 1989, LIEBIGS ANN CHEM, P803
[3] METHYLSULFINYL CARBANION (CH3-SO-CH2-) . FORMATION AND APPLICATIONS TO ORGANIC SYNTHESIS
COREY, EJ
CHAYKOVSKY, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1345 - +
[4] ELLIGER CA, 1989, ACS SYM SER, V387, P188
[5] MINOR PETUNIASTERONES FROM PETUNIA-HYBRIDA
ELLIGER, CA
BENSON, M
LUNDIN, RE
WAISS, AC
[J]. PHYTOCHEMISTRY, 1988, 27 (11) : 3597 - 3603
[6] PETUNIANINES, UNUSUAL STEROIDAL NITROGENOUS BASES FROM PETUNIA-INFLATA
ELLIGER, CA
WONG, RY
BENSON, M
WAISS, AC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (01): : 5 - 6
[7] X-RAY CRYSTAL-STRUCTURE OF PETUNIASTERONE-O, A NOVEL ERGOSTANOID FROM PETUNIA-PARODII
ELLIGER, CA
WONG, RY
BENSON, M
WAISS, AC
[J]. JOURNAL OF NATURAL PRODUCTS, 1989, 52 (06): : 1345 - 1349
[8] PETUNIASTERONES FROM PETUNIA-PARODII AND PETUNIA-INTEGRIFOLIA - UNUSUAL ERGOSTANE-TYPE STEROIDS
ELLIGER, CA
WAISS, AC
WONG, RY
BENSON, M
[J]. PHYTOCHEMISTRY, 1989, 28 (12) : 3443 - 3452
[9] PETUNIASTERONES .2. NOVEL ERGOSTANE-TYPE STEROIDS FROM PETUNIA-HYBRIDA VILM (SOLANACEAE)
ELLIGER, CA
BENSON, M
HADDON, WF
LUNDIN, RE
WAISS, AC
WONG, RY
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01): : 143 - 149
[10] PETUNIASTERONE-N, AN UNUSUAL ERGOSTANOID FROM PETUNIA SPECIES
ELLIGER, CA
HADDON, WF
WAISS, AC
BENSON, M
[J]. JOURNAL OF NATURAL PRODUCTS, 1989, 52 (03): : 576 - 580

← 1 2 3 4 →