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Investigations into the Manzamine Alkaloid Biosynthetic Hypothesis
Author(s) -
Baldwin Jack E.,
Claridge Timothy D. W.,
Culshaw Andrew J.,
Heupel Florian A.,
Lee Victor,
Spring David R.,
Whitehead Roger C.,
Boughtflower Robert J.,
Mutton Ian M.,
Upton Richard J.
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981016)37:19<2661::aid-anie2661>3.0.co;2-d
Subject(s) - alkaloid , intramolecular force , stereochemistry , chemistry , biosynthesis , biochemistry , enzyme
The biomimetic synthesis of a pentacyclic alkaloid (keramaphidin B, 1 ), an intermediate in the biogenetic pathway to the manzamine alkaloids, has been achieved. Compound 1 was formed by an intramolecular Diels–Alder reaction of macrocycle 2 in buffer followed by reduction with NaBH 4 . This reaction provides the first direct expeimental evidence for the authors' biosynthetic hypothesis.