Efficient total synthesis of marine alkaloid (-)-nakadomarin A

Bin Cheng; Fufang Wu; Xiaobao Yang; Yuedong Zhou; Xiaolong Wan; Hongbin Zhai

doi:10.1002/chem.201102101

Efficient total synthesis of marine alkaloid (-)-nakadomarin A

Bin Cheng, Fufang Wu, Xiaobao Yang, Yuedong Zhou, Xiaolong Wan, Hongbin Zhai

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

52 Scopus citations

Abstract

Z's top: For the total synthesis of the marine alkaloid (-)-nakadomarin A, (-)-camphorsulfonic acid assisted, Z-selective, olefin RCM of a monoamine (less polar) rather than a diamine (more polar) was found to be highly practical for constructing the F ring. The ABCD-tetracyclic core was assembled through a novel efficacious PtCl ₂-promoted cascade reaction sequence (see scheme).

Original language	English
Pages (from-to)	12569-12572
Number of pages	4
Journal	Chemistry - A European Journal
Volume	17
Issue number	45
DOIs	https://doi.org/10.1002/chem.201102101
State	Published - 4 Nov 2011
Externally published	Yes

Keywords

Z-selective RCM
alkaloids
cascade reactions
monoamines
total synthesis

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10.1002/chem.201102101

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title = "Efficient total synthesis of marine alkaloid (-)-nakadomarin A",

abstract = "Z's top: For the total synthesis of the marine alkaloid (-)-nakadomarin A, (-)-camphorsulfonic acid assisted, Z-selective, olefin RCM of a monoamine (less polar) rather than a diamine (more polar) was found to be highly practical for constructing the F ring. The ABCD-tetracyclic core was assembled through a novel efficacious PtCl 2-promoted cascade reaction sequence (see scheme).",

keywords = "Z-selective RCM, alkaloids, cascade reactions, monoamines, total synthesis",

author = "Bin Cheng and Fufang Wu and Xiaobao Yang and Yuedong Zhou and Xiaolong Wan and Hongbin Zhai",

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doi = "10.1002/chem.201102101",

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T1 - Efficient total synthesis of marine alkaloid (-)-nakadomarin A

AU - Cheng, Bin

AU - Wu, Fufang

AU - Yang, Xiaobao

AU - Zhou, Yuedong

AU - Wan, Xiaolong

AU - Zhai, Hongbin

PY - 2011/11/4

Y1 - 2011/11/4

N2 - Z's top: For the total synthesis of the marine alkaloid (-)-nakadomarin A, (-)-camphorsulfonic acid assisted, Z-selective, olefin RCM of a monoamine (less polar) rather than a diamine (more polar) was found to be highly practical for constructing the F ring. The ABCD-tetracyclic core was assembled through a novel efficacious PtCl 2-promoted cascade reaction sequence (see scheme).

AB - Z's top: For the total synthesis of the marine alkaloid (-)-nakadomarin A, (-)-camphorsulfonic acid assisted, Z-selective, olefin RCM of a monoamine (less polar) rather than a diamine (more polar) was found to be highly practical for constructing the F ring. The ABCD-tetracyclic core was assembled through a novel efficacious PtCl 2-promoted cascade reaction sequence (see scheme).

KW - Z-selective RCM

KW - alkaloids

KW - cascade reactions

KW - monoamines

KW - total synthesis

UR - https://www.scopus.com/pages/publications/80054887611

U2 - 10.1002/chem.201102101

DO - 10.1002/chem.201102101

M3 - Article

C2 - 21956824

AN - SCOPUS:80054887611

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EP - 12572

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 45

ER -

Efficient total synthesis of marine alkaloid (-)-nakadomarin A

Abstract

Keywords

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