Pd(II)-Mediated Alkynediol Spiroketalization: First Total Synthesis of (−)-Cephalosporolide E and (+)-Cephalosporolide F

Herein we describe a concise assembly of the central 1,6-dioxaspiro[4.4]nonane core of cephalosporolides E/F by employing a Pd-mediated alkynediol cycloisomerization and their total synthesis. On the basis of spectroscopic data and optical rotation values, the absolute configurations of cephalosporo...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-04, Vol.74 (7), p.2842-2845
Main Authors: Ramana, C. V, Suryawanshi, Sharad B, Gonnade, Rajesh G
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Palladium - chemistry
Preparations and properties
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
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Summary:Herein we describe a concise assembly of the central 1,6-dioxaspiro[4.4]nonane core of cephalosporolides E/F by employing a Pd-mediated alkynediol cycloisomerization and their total synthesis. On the basis of spectroscopic data and optical rotation values, the absolute configurations of cephalosporolides E/F were proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo802539z