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

Ichiro Hayakawa; Masami Okamura; Kazuaki Suzuki; Mami Shimanuki; Kizuku Kimura; Takuya Yamada; Takayuki Ohyoshi; Hideo Kigoshi

doi:10.1055/s-0036-1588169

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

Ichiro Hayakawa, Masami Okamura, Kazuaki Suzuki, Mami Shimanuki, Kizuku Kimura, Takuya Yamada, Takayuki Ohyoshi, Hideo Kigoshi

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2958-2970
Number of pages	13
Journal	Synthesis (Germany)
Volume	49
Issue number	13
DOIs	https://doi.org/10.1055/s-0036-1588169
Publication status	Published - Jul 3 2017

Keywords

asymmetric aldol reaction
biselide A
haterumalides
macrolide
regioselective enzymatic hydrolysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1055/s-0036-1588169

Cite this

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title = "Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin",

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.",

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author = "Ichiro Hayakawa and Masami Okamura and Kazuaki Suzuki and Mami Shimanuki and Kizuku Kimura and Takuya Yamada and Takayuki Ohyoshi and Hideo Kigoshi",

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language = "English",

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TY - JOUR

T1 - Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin

AU - Hayakawa, Ichiro

AU - Okamura, Masami

AU - Suzuki, Kazuaki

AU - Shimanuki, Mami

AU - Kimura, Kizuku

AU - Yamada, Takuya

AU - Ohyoshi, Takayuki

AU - Kigoshi, Hideo

PY - 2017/7/3

Y1 - 2017/7/3

N2 - 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.

AB - 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.

KW - asymmetric aldol reaction

KW - biselide A

KW - haterumalides

KW - macrolide

KW - regioselective enzymatic hydrolysis

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U2 - 10.1055/s-0036-1588169

DO - 10.1055/s-0036-1588169

M3 - Article

AN - SCOPUS:85017205548

SN - 0039-7881

VL - 49

SP - 2958

EP - 2970

JO - Synthesis

JF - Synthesis

IS - 13

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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