Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques

Matthew T. Jones; Brett D. Schwartz; Anthony C. Willis; Martin G. Banwell

doi:10.1021/ol901364n

Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques

Matthew T. Jones
, Brett D. Schwartz
, Anthony C. Willis
, Martin G. Banwell

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

34 Citations (Scopus)

Abstract

The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.

Original language	English
Pages (from-to)	3506-3509
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	15
DOIs	https://doi.org/10.1021/ol901364n
Publication status	Published - 6 Aug 2009

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10.1021/ol901364n

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title = "Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques",

abstract = "The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.",

author = "Jones, \{Matthew T.\} and Schwartz, \{Brett D.\} and Willis, \{Anthony C.\} and Banwell, \{Martin G.\}",

year = "2009",

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doi = "10.1021/ol901364n",

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T1 - Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques

AU - Jones, Matthew T.

AU - Schwartz, Brett D.

AU - Willis, Anthony C.

AU - Banwell, Martin G.

PY - 2009/8/6

Y1 - 2009/8/6

N2 - The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.

AB - The pentacyclic framework associated with the alkaloid (-)-lycorine (1) can be assembled in as few as six steps from the enantiomerically pure cis-1,2-dihydrocatechol 3 which is itself readily available on a large scale through the whole-cell biotransformation of bromobenzene. The methodology has been used in developing the first synthesis of compound 2, a derivative of lycorine.

UR - https://www.scopus.com/pages/publications/68149142567

U2 - 10.1021/ol901364n

DO - 10.1021/ol901364n

M3 - Article

SN - 1523-7060

VL - 11

SP - 3506

EP - 3509

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Rapid and enantioselective assembly of the lycorine framework using chemoenzymatic techniques

Abstract

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