Total synthesis of 14,21-diepi-squamocin-K

Chun Wei Liu; Tze Chiun Yeh; Chia Hsiu Chen; Chia Chun Yu; Cheng Sheng Chen; Duen Ren Hou; Jih Hwa Guh

doi:10.1016/j.tet.2013.02.015

Total synthesis of 14,21-diepi-squamocin-K

Chun Wei Liu, Tze Chiun Yeh, Chia Hsiu Chen, Chia Chun Yu, Cheng Sheng Chen, Duen Ren Hou, Jih Hwa Guh

Department of Chemistry

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

6 Scopus citations

Abstract

A new method to prepare annonaceous acetogenins is described in the synthesis of the 14,21-diepimer (14) of squamocin-K. The synthesis utilized the controlled sequence of ring-closing metathesis (RCM) and cross metathesis (CM) reactions to incorporate the stereocenters and skeleton from (3R,4R)-1,5-hexadiene-3,4-diol and 10-chloro-1-decene. The lactone moiety was attached through nucleophilic substitution and achieved the desymmetrization. Inhibitory activities of 14 against human hormone-refractory prostate cancer cell line (PC-3) were also evaluated.

Original language	English
Pages (from-to)	2971-2976
Number of pages	6
Journal	Tetrahedron
Volume	69
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2013.02.015
State	Published - 8 Apr 2013

Keywords

Annonaceous acetogenin
Asymmetric synthesis
C Symmetry
Cross metathesis
Ring-closing metathesis

UN SDGs

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

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10.1016/j.tet.2013.02.015

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title = "Total synthesis of 14,21-diepi-squamocin-K",

abstract = "A new method to prepare annonaceous acetogenins is described in the synthesis of the 14,21-diepimer (14) of squamocin-K. The synthesis utilized the controlled sequence of ring-closing metathesis (RCM) and cross metathesis (CM) reactions to incorporate the stereocenters and skeleton from (3R,4R)-1,5-hexadiene-3,4-diol and 10-chloro-1-decene. The lactone moiety was attached through nucleophilic substitution and achieved the desymmetrization. Inhibitory activities of 14 against human hormone-refractory prostate cancer cell line (PC-3) were also evaluated.",

keywords = "Annonaceous acetogenin, Asymmetric synthesis, C Symmetry, Cross metathesis, Ring-closing metathesis",

author = "Liu, {Chun Wei} and Yeh, {Tze Chiun} and Chen, {Chia Hsiu} and Yu, {Chia Chun} and Chen, {Cheng Sheng} and Hou, {Duen Ren} and Guh, {Jih Hwa}",

note = "Funding Information: This research was supported by the National Science Council ( NSC 98-2119-M-008-001 ), Taiwan. The authors thank Prof. John C. Gilbert, Santa Clara University, for helpful comments. We are grateful to Ms. Ping-YuLin at the Institute of Chemistry, Academia Sinica, and Valuable Instrument Center in National Central University for obtaining mass analysis. ",

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doi = "10.1016/j.tet.2013.02.015",

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T1 - Total synthesis of 14,21-diepi-squamocin-K

AU - Liu, Chun Wei

AU - Yeh, Tze Chiun

AU - Chen, Chia Hsiu

AU - Yu, Chia Chun

AU - Chen, Cheng Sheng

AU - Hou, Duen Ren

AU - Guh, Jih Hwa

N1 - Funding Information: This research was supported by the National Science Council ( NSC 98-2119-M-008-001 ), Taiwan. The authors thank Prof. John C. Gilbert, Santa Clara University, for helpful comments. We are grateful to Ms. Ping-YuLin at the Institute of Chemistry, Academia Sinica, and Valuable Instrument Center in National Central University for obtaining mass analysis.

PY - 2013/4/8

Y1 - 2013/4/8

N2 - A new method to prepare annonaceous acetogenins is described in the synthesis of the 14,21-diepimer (14) of squamocin-K. The synthesis utilized the controlled sequence of ring-closing metathesis (RCM) and cross metathesis (CM) reactions to incorporate the stereocenters and skeleton from (3R,4R)-1,5-hexadiene-3,4-diol and 10-chloro-1-decene. The lactone moiety was attached through nucleophilic substitution and achieved the desymmetrization. Inhibitory activities of 14 against human hormone-refractory prostate cancer cell line (PC-3) were also evaluated.

AB - A new method to prepare annonaceous acetogenins is described in the synthesis of the 14,21-diepimer (14) of squamocin-K. The synthesis utilized the controlled sequence of ring-closing metathesis (RCM) and cross metathesis (CM) reactions to incorporate the stereocenters and skeleton from (3R,4R)-1,5-hexadiene-3,4-diol and 10-chloro-1-decene. The lactone moiety was attached through nucleophilic substitution and achieved the desymmetrization. Inhibitory activities of 14 against human hormone-refractory prostate cancer cell line (PC-3) were also evaluated.

KW - Annonaceous acetogenin

KW - Asymmetric synthesis

KW - C Symmetry

KW - Cross metathesis

KW - Ring-closing metathesis

UR - http://www.scopus.com/inward/record.url?scp=84874665065&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2013.02.015

DO - 10.1016/j.tet.2013.02.015

M3 - 期刊論文

AN - SCOPUS:84874665065

SN - 0040-4020

VL - 69

SP - 2971

EP - 2976

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

Total synthesis of 14,21-diepi-squamocin-K

Abstract

Keywords

UN SDGs

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