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Bioinspired total synthesis of agelastatin A.

ABSTRACT: A one-two punch: two potentially biosynthetically relevant cyclizations of a keramadine analogue give agelastatin A. A diastereoselective C-ring formation, which proceeds through a 5-exo-trig cyclization or a Nazarov cyclization of a red-colored N-acyliminium intermediate, generates the three contiguous stereocenters of the cyclopentane core. A silica gel assisted cyclization of a nagelamide J analogue gives agelastatin A.

SUBMITTER: Reyes JC

PROVIDER: S-EPMC3815442 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Bioinspired total synthesis of agelastatin A.

Reyes Jeremy Chris P JC Romo Daniel D

Angewandte Chemie (International ed. in English) 20120611 28

A one-two punch: two potentially biosynthetically relevant cyclizations of a keramadine analogue give agelastatin A. A diastereoselective C-ring formation, which proceeds through a 5-exo-trig cyclization or a Nazarov cyclization of a red-colored N-acyliminium intermediate, generates the three contiguous stereocenters of the cyclopentane core. A silica gel assisted cyclization of a nagelamide J analogue gives agelastatin A. ...[more]

PMID: 22689447

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