Author:
Kelly Ronald B.,Beckett Barry A.,Eber Jeno,Hung Hing-Kwok,Zamecnik Jiri
Abstract
The cyclization of bicyclooctane systems to tricyclooctane systems is discussed with particular reference to stereochemical aspects as encountered during the total syntheses of ishwarane and trachylobane. Of special interest are the homoallylic cyclizations. A third, convenient synthesis of trachylobane via a reductive homoallylic cyclization is reported.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
21 articles.
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1. Asymmetric Divergent Synthesis of ent-Kaurane-, ent-Atisane-, ent-Beyerane-, ent-Trachylobane-, and ent-Gibberellane-type Diterpenoids;Journal of the American Chemical Society;2022-12-20
2. Total Synthesis and Late‐Stage C−H Oxidations of
ent
‐Trachylobane Natural Products;Angewandte Chemie International Edition;2021-11-27
3. Total Synthesis and Late‐Stage C−H Oxidations of
ent
‐Trachylobane Natural Products;Angewandte Chemie;2021-11-27
4. Divergent Total Synthesis of Euphoranginol C, Euphoranginone D,
ent
‐Trachyloban‐3β‐ol,
ent
‐Trachyloban‐3‐one, Excoecarin E, and
ent
‐16α‐Hydroxy‐atisane‐3‐one;Angewandte Chemie International Edition;2020-08-31
5. Divergent Total Synthesis of Euphoranginol C, Euphoranginone D,
ent
‐Trachyloban‐3β‐ol,
ent
‐Trachyloban‐3‐one, Excoecarin E, and
ent
‐16α‐Hydroxy‐atisane‐3‐one;Angewandte Chemie;2020-08-31