Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework

Fei Tang; Ping Lan; Benoit Bolte; Martin G. Banwell; Jas S. Ward; Anthony C. Willis

doi:10.1021/acs.joc.8b02626

Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework

Fei Tang, Ping Lan, Benoit Bolte, Martin G. Banwell^*, Jas S. Ward, Anthony C. Willis

^*Corresponding author for this work

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

13 Citations (SciVal)

Abstract

A total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels-Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the title compound 4.

Original language	English
Pages (from-to)	14049-14056
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	83
Issue number	22
DOIs	https://doi.org/10.1021/acs.joc.8b02626
Publication status	Published - 16 Nov 2018

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title = "Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework",

abstract = "A total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels-Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the title compound 4.",

author = "Fei Tang and Ping Lan and Benoit Bolte and Banwell, \{Martin G.\} and Ward, \{Jas S.\} and Willis, \{Anthony C.\}",

year = "2018",

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doi = "10.1021/acs.joc.8b02626",

language = "English",

volume = "83",

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journal = "Journal of Organic Chemistry",

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T1 - Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework

AU - Tang, Fei

AU - Lan, Ping

AU - Bolte, Benoit

AU - Banwell, Martin G.

AU - Ward, Jas S.

AU - Willis, Anthony C.

PY - 2018/11/16

Y1 - 2018/11/16

N2 - A total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels-Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the title compound 4.

AB - A total synthesis of the title sesquiterpene 4 is described that starts with the chiral, non-racemic cis-1,2-dihydrocatechol 10 obtained through the whole-cell biotransformation of p-iodotoluene. Compound 10 is elaborated over seven steps, including Negishi cross-coupling and intramolecular Diels-Alder (IMDA) cycloaddition reactions, to ketone 7 that engages in a photochemically promoted 1,3-acyl migration and so affording cyclobutanone 6. Compound 6 was converted over further steps into the title compound 4.

UR - http://www.scopus.com/inward/record.url?scp=85056555739&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b02626

DO - 10.1021/acs.joc.8b02626

M3 - Article

SN - 0022-3263

VL - 83

SP - 14049

EP - 14056

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

Total Synthesis of (+)-Viridianol, a Marine-Derived Sesquiterpene Embodying the Decahydrocyclobuta[ d]indene Framework

Abstract

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