Total Synthesis of (+)-Papuamine:  An Antifungal Pentacyclic Alkaloid from a Marine Sponge, Haliclona sp

The total synthesis of (+)-papuamine, the antipode of the C 2-symmetric, optically active, pentacyclic diamine natural product, starting from a chiral diol is described. The diol is available via an asymmetric Diels−Alder reaction between 1,3-butadiene and di-(−)-menthyl fumarate. The key transforma...

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Published inJournal of organic chemistry Vol. 61; no. 2; pp. 685 - 699
Main Authors Barrett, Anthony G. M, Boys, Mark L, Boehm, Terri L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.01.1996
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CONVENIENT SYNTHESIS
ORGANIC-SYNTHESIS
PALLADIUM
CROSS-COUPLING REACTIONS
REAGENTS
HIGHLY STEREOSELECTIVE SYNTHESIS
DIMETHYL-SULFOXIDE
VINYL HALIDES
NITRO CYCLO OLEFINS
DERIVATIVES
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Summary:The total synthesis of (+)-papuamine, the antipode of the C 2-symmetric, optically active, pentacyclic diamine natural product, starting from a chiral diol is described. The diol is available via an asymmetric Diels−Alder reaction between 1,3-butadiene and di-(−)-menthyl fumarate. The key transformation in the synthesis is an intramolecular Pd(0)-catalyzed (Stille) coupling reaction to form the central 13-membered diazadiene macrocyclic ring.
Bibliography:istex:4B4B875CB4E4983AB1E4D1B409394B8E8AB8779C
Abstract published in Advance ACS Abstracts, January 1, 1996.
ark:/67375/TPS-9ZD95LM9-8
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo951413z