Total synthesis of (-)-nakadomarin A

Mark G. Nilson; Raymond L. Funk

doi:10.1021/ol102079z

Total synthesis of (-)-nakadomarin A

Mark G. Nilson
, Raymond L. Funk

Chemistry

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

64 Scopus citations

Abstract

A concise diastereoselective total synthesis of (-)-nakadomarin A has been completed in 21 steps from d-pyroglutamic acid. Key steps include an enecarbamate Michael addition/furan-N-acyliminium ion cascade cyclization to provide the tetracyclic core and ring-closing alkyne and alkene metatheses to construct the fifteen- and eight-membered azacycles, respectively.

Original language	English (US)
Pages (from-to)	4912-4915
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	21
DOIs	https://doi.org/10.1021/ol102079z
State	Published - Nov 5 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol102079z

Cite this

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title = "Total synthesis of (-)-nakadomarin A",

abstract = "A concise diastereoselective total synthesis of (-)-nakadomarin A has been completed in 21 steps from d-pyroglutamic acid. Key steps include an enecarbamate Michael addition/furan-N-acyliminium ion cascade cyclization to provide the tetracyclic core and ring-closing alkyne and alkene metatheses to construct the fifteen- and eight-membered azacycles, respectively.",

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journal = "Organic Letters",

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AU - Funk, Raymond L.

PY - 2010/11/5

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N2 - A concise diastereoselective total synthesis of (-)-nakadomarin A has been completed in 21 steps from d-pyroglutamic acid. Key steps include an enecarbamate Michael addition/furan-N-acyliminium ion cascade cyclization to provide the tetracyclic core and ring-closing alkyne and alkene metatheses to construct the fifteen- and eight-membered azacycles, respectively.

AB - A concise diastereoselective total synthesis of (-)-nakadomarin A has been completed in 21 steps from d-pyroglutamic acid. Key steps include an enecarbamate Michael addition/furan-N-acyliminium ion cascade cyclization to provide the tetracyclic core and ring-closing alkyne and alkene metatheses to construct the fifteen- and eight-membered azacycles, respectively.

UR - https://www.scopus.com/pages/publications/78049509134

UR - https://www.scopus.com/pages/publications/78049509134#tab=citedBy

U2 - 10.1021/ol102079z

DO - 10.1021/ol102079z

M3 - Article

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AN - SCOPUS:78049509134

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SP - 4912

EP - 4915

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Total synthesis of (-)-nakadomarin A

Abstract

All Science Journal Classification (ASJC) codes

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