Conversion of the Enzymatically Derived (1 S,2 S)-3-Bromocyclohexa-3,5-diene-1,2-diol into Enantiomerically Pure Compounds Embodying the Pentacyclic Framework of Vindoline

Lorenzo V. White; Martin G. Banwell

doi:10.1021/acs.joc.5b02788

Conversion of the Enzymatically Derived (1 S,2 S)-3-Bromocyclohexa-3,5-diene-1,2-diol into Enantiomerically Pure Compounds Embodying the Pentacyclic Framework of Vindoline

Lorenzo V. White
, Martin G. Banwell^*

^*Corresponding author for this work

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

21 Citations (Scopus)

Abstract

The enzymatically derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 17 steps into compounds 8 and 32, each of which embodies the pentacyclic framework and much of the functionality associated with the alkaloid vindoline (3). This work sets the stage for effecting the conversion of the related metabolite (1S,6R)-5-ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid (4) into compound 3, the latter being a biogenetic precursor to the clinically significant anticancer agents vinblastine and vincristine. (Chemical Equation Presented).

Original language	English
Pages (from-to)	1617-1626
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	81
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.5b02788
Publication status	Published - 19 Feb 2016

Access to Document

10.1021/acs.joc.5b02788

Cite this

@article{39720db276204c629be4727e8b15fa44,

title = "Conversion of the Enzymatically Derived (1 S,2 S)-3-Bromocyclohexa-3,5-diene-1,2-diol into Enantiomerically Pure Compounds Embodying the Pentacyclic Framework of Vindoline",

abstract = "The enzymatically derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 17 steps into compounds 8 and 32, each of which embodies the pentacyclic framework and much of the functionality associated with the alkaloid vindoline (3). This work sets the stage for effecting the conversion of the related metabolite (1S,6R)-5-ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid (4) into compound 3, the latter being a biogenetic precursor to the clinically significant anticancer agents vinblastine and vincristine. (Chemical Equation Presented).",

author = "White, \{Lorenzo V.\} and Banwell, \{Martin G.\}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = feb,

day = "19",

doi = "10.1021/acs.joc.5b02788",

language = "English",

volume = "81",

pages = "1617--1626",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - Conversion of the Enzymatically Derived (1 S,2 S)-3-Bromocyclohexa-3,5-diene-1,2-diol into Enantiomerically Pure Compounds Embodying the Pentacyclic Framework of Vindoline

AU - White, Lorenzo V.

AU - Banwell, Martin G.

PY - 2016/2/19

Y1 - 2016/2/19

N2 - The enzymatically derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 17 steps into compounds 8 and 32, each of which embodies the pentacyclic framework and much of the functionality associated with the alkaloid vindoline (3). This work sets the stage for effecting the conversion of the related metabolite (1S,6R)-5-ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid (4) into compound 3, the latter being a biogenetic precursor to the clinically significant anticancer agents vinblastine and vincristine. (Chemical Equation Presented).

AB - The enzymatically derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 17 steps into compounds 8 and 32, each of which embodies the pentacyclic framework and much of the functionality associated with the alkaloid vindoline (3). This work sets the stage for effecting the conversion of the related metabolite (1S,6R)-5-ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid (4) into compound 3, the latter being a biogenetic precursor to the clinically significant anticancer agents vinblastine and vincristine. (Chemical Equation Presented).

UR - https://www.scopus.com/pages/publications/84959018007

U2 - 10.1021/acs.joc.5b02788

DO - 10.1021/acs.joc.5b02788

M3 - Article

SN - 0022-3263

VL - 81

SP - 1617

EP - 1626

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

Conversion of the Enzymatically Derived (1 S,2 S)-3-Bromocyclohexa-3,5-diene-1,2-diol into Enantiomerically Pure Compounds Embodying the Pentacyclic Framework of Vindoline

Abstract

Access to Document

Other files and links

Fingerprint

Cite this