An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

Michael P. Cassidy; Ayse Daut Özdemir; Albert Padwa

doi:10.1021/ol0501323

An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

Michael P. Cassidy
, Ayse Daut Özdemir
, Albert Padwa^*

^*Bu çalışma için yazışmadan sorumlu yazar

Emory University

Araştırma sonucu: Dergiye katkı › Makale › bilirkişi

34 Atıf (Scopus)

Özet

(Chemical Equation Presented) A one-pot procedure was developed to efficiently prepare hexahydroindolinones containing a tethered furan ring. Reaction of a furanyl azide with Bu₃P delivered the iminophosphorane, which was allowed to react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (±)-selaginoidine.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	1339-1342
Sayfa sayısı	4
Dergi	Organic Letters
Hacim	7
Basın numarası	7
DOI'lar	https://doi.org/10.1021/ol0501323
Yayın durumu	Yayınlandı - 31 Mar 2005
Harici olarak yayınlandı	Evet

Finansman

Finansörler	Finansör numarası
National Institute of General Medical Sciences	R01GM059384

Belgeye Erişim

10.1021/ol0501323

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

@article{574f5b3c08c144fc8f36b18b19117ea8,

title = "An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine",

abstract = "(Chemical Equation Presented) A one-pot procedure was developed to efficiently prepare hexahydroindolinones containing a tethered furan ring. Reaction of a furanyl azide with Bu3P delivered the iminophosphorane, which was allowed to react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (±)-selaginoidine.",

author = "Cassidy, \{Michael P.\} and {\"O}zdemir, \{Ayse Daut\} and Albert Padwa",

year = "2005",

month = mar,

day = "31",

doi = "10.1021/ol0501323",

language = "English",

volume = "7",

pages = "1339--1342",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

AU - Cassidy, Michael P.

AU - Özdemir, Ayse Daut

AU - Padwa, Albert

PY - 2005/3/31

Y1 - 2005/3/31

N2 - (Chemical Equation Presented) A one-pot procedure was developed to efficiently prepare hexahydroindolinones containing a tethered furan ring. Reaction of a furanyl azide with Bu3P delivered the iminophosphorane, which was allowed to react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (±)-selaginoidine.

AB - (Chemical Equation Presented) A one-pot procedure was developed to efficiently prepare hexahydroindolinones containing a tethered furan ring. Reaction of a furanyl azide with Bu3P delivered the iminophosphorane, which was allowed to react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (±)-selaginoidine.

UR - https://www.scopus.com/pages/publications/17444423725

U2 - 10.1021/ol0501323

DO - 10.1021/ol0501323

M3 - Article

C2 - 15787501

AN - SCOPUS:17444423725

SN - 1523-7060

VL - 7

SP - 1339

EP - 1342

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

An aza-wittig/π-furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine

Özet

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

Parmak izi

Alıntı Yap