Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

Kenji Sugimoto; Kazuki Toyoshima; Shiori Nonaka; Kenta Kotaki; Hirofumi Ueda; Hidetoshi Tokuyama

doi:10.1002/anie.201303067

Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

Kenji Sugimoto, Kazuki Toyoshima, Shiori Nonaka, Kenta Kotaki, Hirofumi Ueda, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

79 Citations (Scopus)

Abstract

'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.

Original language	English
Pages (from-to)	7168-7171
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	28
DOIs	https://doi.org/10.1002/anie.201303067
Publication status	Published - 2013 Jul 8

Keywords

alkaloids
cyclization
gold
natural products
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201303067

Cite this

@article{d28db41946c74cc8b81363cc488c0b9d,

title = "Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization",

abstract = "'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.",

keywords = "alkaloids, cyclization, gold, natural products, total synthesis",

author = "Kenji Sugimoto and Kazuki Toyoshima and Shiori Nonaka and Kenta Kotaki and Hirofumi Ueda and Hidetoshi Tokuyama",

year = "2013",

month = jul,

day = "8",

doi = "10.1002/anie.201303067",

language = "English",

volume = "52",

pages = "7168--7171",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "28",

}

TY - JOUR

T1 - Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

AU - Sugimoto, Kenji

AU - Toyoshima, Kazuki

AU - Nonaka, Shiori

AU - Kotaki, Kenta

AU - Ueda, Hirofumi

AU - Tokuyama, Hidetoshi

PY - 2013/7/8

Y1 - 2013/7/8

N2 - 'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.

AB - 'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.

KW - alkaloids

KW - cyclization

KW - gold

KW - natural products

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84880143408&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880143408&partnerID=8YFLogxK

U2 - 10.1002/anie.201303067

DO - 10.1002/anie.201303067

M3 - Article

C2 - 23744784

AN - SCOPUS:84880143408

VL - 52

SP - 7168

EP - 7171

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 28

ER -

Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this