Asymmetric Total Synthesis of (+)-(3E)-Pinnatifidenyne via Abnormally Regioselective Pd(0)-Catalyzed Endocyclization

Hyun Su Kim; Taewoo Kim; Jungmin Ahn; Hwayoung Yun; Changjin Lim; Jaebong Jang; Jaehoon Sim; Hongchan An; Young Joon Surh; Jeeyeon Lee; Young Ger Suh

doi:10.1021/acs.joc.7b02937

Asymmetric Total Synthesis of (+)-(3E)-Pinnatifidenyne via Abnormally Regioselective Pd(0)-Catalyzed Endocyclization

Hyun Su Kim
, Taewoo Kim
, Jungmin Ahn
, Hwayoung Yun
, Changjin Lim
, Jaebong Jang
, Jaehoon Sim
, Hongchan An
, Young Joon Surh
, Jeeyeon Lee
, Young Ger Suh

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

8 Citations (Scopus)

Abstract

The asymmetric total synthesis of the marine natural product (+)-(3E)-pinnatifidenyne was accomplished. The key features of the synthesis involve the construction of an eight-membered cyclic ether by the abnormally regioselective Pd(0)-catalyzed cyclization, the installation of a double bond in the oxocene skeleton by sequential in situ deconjugative isomerization, and the efficient introduction of the crucial chloride mediated by the substrate-controlled diastereoselective reduction.

Original language	English
Pages (from-to)	1997-2005
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	83
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.7b02937
Publication status	Published - 16 Feb 2018

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

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10.1021/acs.joc.7b02937

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title = "Asymmetric Total Synthesis of (+)-(3E)-Pinnatifidenyne via Abnormally Regioselective Pd(0)-Catalyzed Endocyclization",

abstract = "The asymmetric total synthesis of the marine natural product (+)-(3E)-pinnatifidenyne was accomplished. The key features of the synthesis involve the construction of an eight-membered cyclic ether by the abnormally regioselective Pd(0)-catalyzed cyclization, the installation of a double bond in the oxocene skeleton by sequential in situ deconjugative isomerization, and the efficient introduction of the crucial chloride mediated by the substrate-controlled diastereoselective reduction.",

author = "Kim, \{Hyun Su\} and Taewoo Kim and Jungmin Ahn and Hwayoung Yun and Changjin Lim and Jaebong Jang and Jaehoon Sim and Hongchan An and Surh, \{Young Joon\} and Jeeyeon Lee and Suh, \{Young Ger\}",

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doi = "10.1021/acs.joc.7b02937",

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T1 - Asymmetric Total Synthesis of (+)-(3E)-Pinnatifidenyne via Abnormally Regioselective Pd(0)-Catalyzed Endocyclization

AU - Kim, Hyun Su

AU - Kim, Taewoo

AU - Ahn, Jungmin

AU - Yun, Hwayoung

AU - Lim, Changjin

AU - Jang, Jaebong

AU - Sim, Jaehoon

AU - An, Hongchan

AU - Surh, Young Joon

AU - Lee, Jeeyeon

AU - Suh, Young Ger

PY - 2018/2/16

Y1 - 2018/2/16

N2 - The asymmetric total synthesis of the marine natural product (+)-(3E)-pinnatifidenyne was accomplished. The key features of the synthesis involve the construction of an eight-membered cyclic ether by the abnormally regioselective Pd(0)-catalyzed cyclization, the installation of a double bond in the oxocene skeleton by sequential in situ deconjugative isomerization, and the efficient introduction of the crucial chloride mediated by the substrate-controlled diastereoselective reduction.

AB - The asymmetric total synthesis of the marine natural product (+)-(3E)-pinnatifidenyne was accomplished. The key features of the synthesis involve the construction of an eight-membered cyclic ether by the abnormally regioselective Pd(0)-catalyzed cyclization, the installation of a double bond in the oxocene skeleton by sequential in situ deconjugative isomerization, and the efficient introduction of the crucial chloride mediated by the substrate-controlled diastereoselective reduction.

UR - https://www.scopus.com/pages/publications/85042202629

U2 - 10.1021/acs.joc.7b02937

DO - 10.1021/acs.joc.7b02937

M3 - Article

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AN - SCOPUS:85042202629

SN - 0022-3263

VL - 83

SP - 1997

EP - 2005

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

Asymmetric Total Synthesis of (+)-(3E)-Pinnatifidenyne via Abnormally Regioselective Pd(0)-Catalyzed Endocyclization

Abstract

Bibliographical note

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