Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A

Joseph Sisko; James R. Henry; Steven M. Weinreb

doi:10.1021/jo00070a035

Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A

Joseph Sisko
, James R. Henry
, Steven M. Weinreb

Chemistry

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

82 Scopus citations

Abstract

An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.

Original language	English (US)
Pages (from-to)	4945-4951
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	58
Issue number	18
DOIs	https://doi.org/10.1021/jo00070a035
State	Published - Jan 1 1993

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

All Science Journal Classification (ASJC) codes

Organic Chemistry

Access to Document

10.1021/jo00070a035

Cite this

@article{c13825c8a4674defb21d73e68e67a7eb,

title = "Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A",

abstract = "An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.",

author = "Joseph Sisko and Henry, \{James R.\} and Weinreb, \{Steven M.\}",

year = "1993",

month = jan,

day = "1",

doi = "10.1021/jo00070a035",

language = "English (US)",

volume = "58",

pages = "4945--4951",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A

AU - Sisko, Joseph

AU - Henry, James R.

AU - Weinreb, Steven M.

PY - 1993/1/1

Y1 - 1993/1/1

N2 - An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.

AB - An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.

UR - https://www.scopus.com/pages/publications/0001286183

UR - https://www.scopus.com/pages/publications/0001286183#tab=citedBy

U2 - 10.1021/jo00070a035

DO - 10.1021/jo00070a035

M3 - Article

AN - SCOPUS:0001286183

SN - 0022-3263

VL - 58

SP - 4945

EP - 4951

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A

Abstract

UN SDGs

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this