An attempted total synthesis of lysergic acid via an alkene/n-sulfonylimine cyclization

Janet L. Ralbovsky; Paul M. Scola; Eiichi Sugino; Carolina Burgos-Garcia; Steven M. Weinreb; Masood Parvez

doi:10.3987/com-96-7493

An attempted total synthesis of lysergic acid via an alkene/n-sulfonylimine cyclization

Janet L. Ralbovsky, Paul M. Scola, Eiichi Sugino, Carolina Burgos-Garcia, Steven M. Weinreb, Masood Parvez

Chemistry

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

15 Scopus citations

Abstract

Lewis acid-promoted cyclization of the N-tosylimine derived from aldehyde alkene (18) affords an interesting rearranged seven-membered ring tricycle (21) rather than the expected intermediate containing the lysergic acid skeleton.

Original language	English (US)
Pages (from-to)	1497-1512
Number of pages	16
Journal	Heterocycles
Volume	43
Issue number	7
DOIs	https://doi.org/10.3987/com-96-7493
State	Published - 1996

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "An attempted total synthesis of lysergic acid via an alkene/n-sulfonylimine cyclization",

abstract = "Lewis acid-promoted cyclization of the N-tosylimine derived from aldehyde alkene (18) affords an interesting rearranged seven-membered ring tricycle (21) rather than the expected intermediate containing the lysergic acid skeleton.",

author = "Ralbovsky, {Janet L.} and Scola, {Paul M.} and Eiichi Sugino and Carolina Burgos-Garcia and Weinreb, {Steven M.} and Masood Parvez",

year = "1996",

doi = "10.3987/com-96-7493",

language = "English (US)",

volume = "43",

pages = "1497--1512",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "7",

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T1 - An attempted total synthesis of lysergic acid via an alkene/n-sulfonylimine cyclization

AU - Ralbovsky, Janet L.

AU - Scola, Paul M.

AU - Sugino, Eiichi

AU - Burgos-Garcia, Carolina

AU - Weinreb, Steven M.

AU - Parvez, Masood

PY - 1996

Y1 - 1996

N2 - Lewis acid-promoted cyclization of the N-tosylimine derived from aldehyde alkene (18) affords an interesting rearranged seven-membered ring tricycle (21) rather than the expected intermediate containing the lysergic acid skeleton.

AB - Lewis acid-promoted cyclization of the N-tosylimine derived from aldehyde alkene (18) affords an interesting rearranged seven-membered ring tricycle (21) rather than the expected intermediate containing the lysergic acid skeleton.

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U2 - 10.3987/com-96-7493

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M3 - Article

AN - SCOPUS:0345010930

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VL - 43

SP - 1497

EP - 1512

JO - Heterocycles

JF - Heterocycles

IS - 7

ER -

An attempted total synthesis of lysergic acid via an alkene/n-sulfonylimine cyclization

Abstract

All Science Journal Classification (ASJC) codes

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