Flexible access to monoterpenoid indole alkaloids using a cyclopentanoid chiral building block

Masato Hayashi; Keiichi Motosawa; Atsushi Satoh; Masatoshi Shibuya; Kunio Ogasawara; Yoshiharu Iwabuchi

doi:10.3987/COM-08-S(F)120

Flexible access to monoterpenoid indole alkaloids using a cyclopentanoid chiral building block

Masato Hayashi, Keiichi Motosawa, Atsushi Satoh, Masatoshi Shibuya, Kunio Ogasawara, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

13 Citations (Scopus)

Abstract

Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R- dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.

Original language	English
Pages (from-to)	855-863
Number of pages	9
Journal	Heterocycles
Volume	77
Issue number	2
DOIs	https://doi.org/10.3987/COM-08-S(F)120
Publication status	Published - 2009 Feb 1

Keywords

Chiral Building Block
Diastereocontrolled Synthesis
Enantiocontrolled Synthesis
Monoterpenoid Indole Alkaloid
Total Synthesis

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-08-S(F)120

Cite this

@article{2abd8627bd854defa7da925f2ddd43ef,

title = "Flexible access to monoterpenoid indole alkaloids using a cyclopentanoid chiral building block",

abstract = "Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R- dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.",

keywords = "Chiral Building Block, Diastereocontrolled Synthesis, Enantiocontrolled Synthesis, Monoterpenoid Indole Alkaloid, Total Synthesis",

author = "Masato Hayashi and Keiichi Motosawa and Atsushi Satoh and Masatoshi Shibuya and Kunio Ogasawara and Yoshiharu Iwabuchi",

year = "2009",

month = feb,

day = "1",

doi = "10.3987/COM-08-S(F)120",

language = "English",

volume = "77",

pages = "855--863",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "2",

}

TY - JOUR

T1 - Flexible access to monoterpenoid indole alkaloids using a cyclopentanoid chiral building block

AU - Hayashi, Masato

AU - Motosawa, Keiichi

AU - Satoh, Atsushi

AU - Shibuya, Masatoshi

AU - Ogasawara, Kunio

AU - Iwabuchi, Yoshiharu

PY - 2009/2/1

Y1 - 2009/2/1

N2 - Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R- dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.

AB - Expedient, diasterocontrolled transformations of 1 to the key synthetic intermediate of corynanthe, iboga, and aspidosperma-class of monoterpenoid indole alkaloids which led up to a formal synthesis of (+)-20R- dihydrocleavamine, (-)-eburnamonine, and a total synthesis of (+)-aspidospermidine (2) have been demonstrated.

KW - Chiral Building Block

KW - Diastereocontrolled Synthesis

KW - Enantiocontrolled Synthesis

KW - Monoterpenoid Indole Alkaloid

KW - Total Synthesis

UR - http://www.scopus.com/inward/record.url?scp=77955675175&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77955675175&partnerID=8YFLogxK

U2 - 10.3987/COM-08-S(F)120

DO - 10.3987/COM-08-S(F)120

M3 - Article

AN - SCOPUS:77955675175

SN - 0385-5414

VL - 77

SP - 855

EP - 863

JO - Heterocycles

JF - Heterocycles

IS - 2

ER -

Flexible access to monoterpenoid indole alkaloids using a cyclopentanoid chiral building block

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this