AN END-GAME STRATEGY FOR CONSTRUCTION OF THE G-H-I RINGS OF PENITREM-D, A TREMORGENIC INDOLE ALKALOID

被引：17

作者：

SMITH, AB ^{[1
]}

OHTA, M ^{[1
]}

CLARK, WM ^{[1
]}

LEAHY, JW ^{[1
]}

机构：

[1] UNIV PENN, MONELL CHEM SENSES CTR, PHILADELPHIA, PA 19104 USA

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)93371-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic approach to the G-H-I ring system of penitrem D has been developed in a model study. To generate the requisite carbon framework, the Stork protocol was utilized for coupling of a scalemic metalloenamine with an epoxide derived from D-glyceraldehyde. Pyran ring formation was then effected via BF3.OEt2-promoted cyclization of a delta-hydroxy allylic acetate.

引用

页码：3033 / 3036

页数：4

共 3 条

[1] TREMORGENIC INDOLE ALKALOIDS .9. ASYMMETRIC CONSTRUCTION OF AN ADVANCED F-G-H-RING LACTONE PRECURSOR FOR THE SYNTHESIS OF PENITREM-D
SMITH, AB
NOLEN, EG
SHIRAI, R
BLASE, FR
OHTA, M
CHIDA, N
HARTZ, RA
FITCH, DM
CLARK, WM
SPRENGELER, PA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24): : 7837 - 7848
[2] TREMORGENIC INDOLE ALKALOID STUDIES .6. PREPARATION OF AN ADVANCED INTERMEDIATE FOR THE SYNTHESIS OF PENITREM-D - SYNTHESIS OF AN INDOLE-OXOCANE
SMITH, AB
HASELTINE, JN
VISNICK, M
[J]. TETRAHEDRON, 1989, 45 (08) : 2431 - 2449
[3] Tremorgenic indole alkaloids, studies directed toward the assembly of the A, F, and I rings of penitrem D: Observation of an unexpected stereochemical outcome
Smith, AB
Kanoh, N
Minakawa, N
Rainier, JD
Blase, FR
Hartz, RA
[J]. ORGANIC LETTERS, 1999, 1 (08) : 1263 - 1266

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