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

Authors
SMITH AB OHTA M CLARK WM LEAHY JW
Citation
Ab. Smith et al., AN END-GAME STRATEGY FOR CONSTRUCTION OF THE G-H-I RINGS OF PENITREM-D, A TREMORGENIC INDOLE ALKALOID, Tetrahedron letters, 34(19), 1993, pp. 3033-3036
Citations number
44
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
19
Year of publication
1993
Pages
3033 - 3036
Database
ISI
SICI code
0040-4039(1993)34:19<3033:AESFCO>2.0.ZU;2-8
Abstract
A synthetic approach to the G-H-I ring system of penitrem D has been d eveloped in a model study. To generate the requisite carbon framework, the Stork protocol was utilized for coupling of a scalemic metalloena mine with an epoxide derived from D-glyceraldehyde. Pyran ring formati on was then effected via BF3.OEt2-promoted cyclization of a delta-hydr oxy allylic acetate.