A Biomimetic Approach to the Discorhabdin Alkaloids:  Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D

The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 64; no. 1; pp. 16 - 22
Main Authors Aubart, Kelly Marshall, Heathcock, Clayton H
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.01.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SPONGE PRIANOS-MELANOS
SULFUR-CONTAINING ALKALOIDS
FORMAL TOTAL SYNTHESES
ISOBATZELLINE-C
A-D
GENUS LATRUNCULIA
CYTOTOXIC PIGMENT
BATZELLINE-C
DERIVATIVES
MAKALUVAMINE-D
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Summary:The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to give enone 46. Bromination at the α position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.
Bibliography:istex:6AB9EC8EC39A213CDF3124936E68D85B7BC4C0E9
ark:/67375/TPS-J9JNMJFS-P
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9815397