Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B | Zendy

Dieter Enders | Zendy; Achim Lenzen | Zendy; Michael Backes | Zendy; Carsten F. Janeck | Zendy; Kelly K. Catlin | Zendy; MarieIsabelle Lannou | Zendy; Jan Runsink | Zendy; Gerhard Raabe | Zendy

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Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

Author(s) -

Dieter Enders,

Achim Lenzen,

Michael Backes,

Carsten F. Janeck,

Kelly K. Catlin,

MarieIsabelle Lannou,

Jan Runsink,

Gerhard Raabe

Publication year - 2005

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo0518093

Subject(s) - stereochemistry , chemistry , intramolecular force , total synthesis , bicyclic molecule , dihydroxylation , metathesis , ketone , ring closing metathesis , amaryllidaceae alkaloids , electrophile , enantioselective synthesis , organic chemistry , alkaloid , catalysis , polymerization , polymer

[structure: see text] The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epi-aglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee > or = 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

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