Synthesis 2017; 49(13): 2958-2970
DOI: 10.1055/s-0036-1588169
paper
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin

Ichiro Hayakawa*
a  Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Masami Okamura
b  Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-857, Japan   Email: ichiro.hayakawa@okayama-u.ac.jp   Email: kigoshi@chem.tsukuba.ac.jp
,
Kazuaki Suzuki
b  Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-857, Japan   Email: ichiro.hayakawa@okayama-u.ac.jp   Email: kigoshi@chem.tsukuba.ac.jp
,
Mami Shimanuki
b  Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-857, Japan   Email: ichiro.hayakawa@okayama-u.ac.jp   Email: kigoshi@chem.tsukuba.ac.jp
,
Kizuku Kimura
b  Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-857, Japan   Email: ichiro.hayakawa@okayama-u.ac.jp   Email: kigoshi@chem.tsukuba.ac.jp
,
Takuya Yamada
b  Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-857, Japan   Email: ichiro.hayakawa@okayama-u.ac.jp   Email: kigoshi@chem.tsukuba.ac.jp
,
Takayuki Ohyoshi
b  Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-857, Japan   Email: ichiro.hayakawa@okayama-u.ac.jp   Email: kigoshi@chem.tsukuba.ac.jp
,
Hideo Kigoshi*
b  Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-857, Japan   Email: ichiro.hayakawa@okayama-u.ac.jp   Email: kigoshi@chem.tsukuba.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 26 February 2017

Accepted after revision: 13 March 2017

Publication Date:
06 April 2017 (online)


Abstract

The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereoselective introduction of a C3 oxygen functional group.

Supporting Information

 
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