First total syntheses of dihydroflustramine C and flustramine E, alkaloids from the marine bryozoan Flustra foliacea

We have developed a simple and practical method for providing the common tricyclic skeleton of physostigmine type alkaloids, and demonstrated its utility for indole alkaloid synthesis. Thus, we achieved the first total syntheses of (±)-dihydroflustramine C and (±)-flustramine E, as well as the total...

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Bibliographic Details
Published inTetrahedron Vol. 58; no. 8; pp. 1479 - 1484
Main Authors Morales-Rı́os, Martha S, Suárez-Castillo, Oscar R, Joseph-Nathan, Pedro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.02.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
dihydroflustramine C
flustramine E
indole alkaloids
Physical Sciences
Science & Technology
total synthesis
indole alkaloids
total synthesis
dihydroflustramine C
flustramine E
DEBROMOFLUSTRAMINE-B
(+/-)-DEBROMOFLUSTRAMINE-B
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Summary:We have developed a simple and practical method for providing the common tricyclic skeleton of physostigmine type alkaloids, and demonstrated its utility for indole alkaloid synthesis. Thus, we achieved the first total syntheses of (±)-dihydroflustramine C and (±)-flustramine E, as well as the total syntheses of their debromoanalogues from the corresponding 2-hydroxyindolenines in five steps with 31, 27, 39 and 23% overall yields, respectively. The structures of some intermediates were confirmed by single crystal X-ray diffraction analyses. The syntheses were accomplished in five steps with 31% and 27% overall yields, respectively.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00011-X