A chemoenzymatic synthesis of the carbobicyclic core associated with CP-225,917 and CP-263,114 (phomoidrides A and B)

M. G. Banwell; K. J. McRae; A. C. Willis

doi:10.1039/b105376k

A chemoenzymatic synthesis of the carbobicyclic core associated with CP-225,917 and CP-263,114 (phomoidrides A and B)

M. G. Banwell^*, K. J. McRae, A. C. Willis

^*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

The bromobenzene-derived and enantiopure cis-1,2-dihydrocatechol 3 has been converted, via a reaction sequence involving Diels-Alder cycloaddition, anionic oxy-Cope rearrangement and Wolff ring-contraction steps, into compound 4 and epimer 24, which embody key structural elements associated with the nonadride-type natural products CP-225,917 (1) and CP-263,114 (2).

Original language	English
Pages (from-to)	2194-2203
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
Volume	1
Issue number	18
DOIs	https://doi.org/10.1039/b105376k
Publication status	Published - 2001

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abstract = "The bromobenzene-derived and enantiopure cis-1,2-dihydrocatechol 3 has been converted, via a reaction sequence involving Diels-Alder cycloaddition, anionic oxy-Cope rearrangement and Wolff ring-contraction steps, into compound 4 and epimer 24, which embody key structural elements associated with the nonadride-type natural products CP-225,917 (1) and CP-263,114 (2).",

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AU - McRae, K. J.

AU - Willis, A. C.

PY - 2001

Y1 - 2001

N2 - The bromobenzene-derived and enantiopure cis-1,2-dihydrocatechol 3 has been converted, via a reaction sequence involving Diels-Alder cycloaddition, anionic oxy-Cope rearrangement and Wolff ring-contraction steps, into compound 4 and epimer 24, which embody key structural elements associated with the nonadride-type natural products CP-225,917 (1) and CP-263,114 (2).

AB - The bromobenzene-derived and enantiopure cis-1,2-dihydrocatechol 3 has been converted, via a reaction sequence involving Diels-Alder cycloaddition, anionic oxy-Cope rearrangement and Wolff ring-contraction steps, into compound 4 and epimer 24, which embody key structural elements associated with the nonadride-type natural products CP-225,917 (1) and CP-263,114 (2).

UR - https://www.scopus.com/pages/publications/0034741047

U2 - 10.1039/b105376k

DO - 10.1039/b105376k

M3 - Article

SN - 1472-7781

VL - 1

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 18

ER -

A chemoenzymatic synthesis of the carbobicyclic core associated with CP-225,917 and CP-263,114 (phomoidrides A and B)

Abstract

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