Synlett 2014; 25(16): 2337-2340
DOI: 10.1055/s-0034-1378562
letter
© Georg Thieme Verlag Stuttgart · New York

Studies toward the Second-Generation Synthesis of Epolactaene: Highly Stereoselective Construction of the Epoxy-γ-Lactam Moiety

Kouta Tajima
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan   Fax: +81(42)4958633   Email: hkogen@my-pharm.ac.jp
,
Yoshifumi Umehara
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan   Fax: +81(42)4958633   Email: hkogen@my-pharm.ac.jp
,
Kenichi Kobayashi
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan   Fax: +81(42)4958633   Email: hkogen@my-pharm.ac.jp
,
Hiroshi Kogen*
Graduate School of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan   Fax: +81(42)4958633   Email: hkogen@my-pharm.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 11 June 2014

Accepted after revision: 08 July 2014

Publication Date:
11 August 2014 (online)


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Abstract

Highly stereoselective synthesis of the epoxy-γ-lactam moiety toward the second-generation total synthesis of epolactaene was achieved via an E-selective Horner–Wadsworth–Emmons reaction using our new reagent and diastereoselective epoxidation of an allyl diol with VO(acac)2 and TBHP.