Chemoenzymatic routes to enantiomerically enriched and polyoxygenated perhydro-3,5a-methanoindeno[4,5- c]furans related to the tashironin class of sesquiterpenes

Mukesh K. Sharma; Martin G. Banwell; Anthony C. Willis

doi:10.1021/acs.joc.5b00303

Chemoenzymatic routes to enantiomerically enriched and polyoxygenated perhydro-3,5a-methanoindeno[4,5- c]furans related to the tashironin class of sesquiterpenes

Mukesh K. Sharma, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

The alcohol 12, which is available in eight steps from the enzymatically derived cis-1,2-dihydrocatechol 8, engages in an intramolecular alkoxy radical-mediated remote functionalization reaction to form the tetrahydrofuran 13, thus establishing the perhydro-3,5a-methanoindeno[4,5-c]furan framework associated with the biologically active tashironins. Various manipulations of compound 13 and certain derivatives allow for the formation of compounds bearing strong structural resemblances to the title natural products.

Original language	English
Pages (from-to)	2930-2936
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	80
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.5b00303
Publication status	Published - 6 Mar 2015

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title = "Chemoenzymatic routes to enantiomerically enriched and polyoxygenated perhydro-3,5a-methanoindeno[4,5- c]furans related to the tashironin class of sesquiterpenes",

abstract = "The alcohol 12, which is available in eight steps from the enzymatically derived cis-1,2-dihydrocatechol 8, engages in an intramolecular alkoxy radical-mediated remote functionalization reaction to form the tetrahydrofuran 13, thus establishing the perhydro-3,5a-methanoindeno[4,5-c]furan framework associated with the biologically active tashironins. Various manipulations of compound 13 and certain derivatives allow for the formation of compounds bearing strong structural resemblances to the title natural products.",

author = "Sharma, \{Mukesh K.\} and Banwell, \{Martin G.\} and Willis, \{Anthony C.\}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

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doi = "10.1021/acs.joc.5b00303",

language = "English",

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AU - Sharma, Mukesh K.

AU - Banwell, Martin G.

AU - Willis, Anthony C.

PY - 2015/3/6

Y1 - 2015/3/6

N2 - The alcohol 12, which is available in eight steps from the enzymatically derived cis-1,2-dihydrocatechol 8, engages in an intramolecular alkoxy radical-mediated remote functionalization reaction to form the tetrahydrofuran 13, thus establishing the perhydro-3,5a-methanoindeno[4,5-c]furan framework associated with the biologically active tashironins. Various manipulations of compound 13 and certain derivatives allow for the formation of compounds bearing strong structural resemblances to the title natural products.

AB - The alcohol 12, which is available in eight steps from the enzymatically derived cis-1,2-dihydrocatechol 8, engages in an intramolecular alkoxy radical-mediated remote functionalization reaction to form the tetrahydrofuran 13, thus establishing the perhydro-3,5a-methanoindeno[4,5-c]furan framework associated with the biologically active tashironins. Various manipulations of compound 13 and certain derivatives allow for the formation of compounds bearing strong structural resemblances to the title natural products.

UR - https://www.scopus.com/pages/publications/84924325584

U2 - 10.1021/acs.joc.5b00303

DO - 10.1021/acs.joc.5b00303

M3 - Article

SN - 0022-3263

VL - 80

SP - 2930

EP - 2936

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Chemoenzymatic routes to enantiomerically enriched and polyoxygenated perhydro-3,5a-methanoindeno[4,5- c]furans related to the tashironin class of sesquiterpenes

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