Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B

Qi Chen; Martin G. Banwell; Michael G. Gardiner; Ping Lan; Shen Tan

doi:10.1021/acs.joc.4c01738

Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B

Qi Chen, Martin G. Banwell^*, Michael G. Gardiner, Ping Lan, Shen Tan^*

^*Corresponding author for this work

Research School of Chemistry

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

1 Citation (Scopus)

Abstract

The racemic modification of the α-tropolone-containing sesquiterpene olaximbriside A [viz. (±)-4)] has been prepared over 12 steps from the readily accessible decalin derivative 12. The last two of these steps involve a fully regiocontrolled substitution reaction of bromotropone 24. The aromatization of a stereoisomeric and co-produced form of compound 12 has provided (±)-olaximbriside B [(±)-5)].

Original language	English
Pages (from-to)	13530-13539
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	89
Issue number	18
DOIs	https://doi.org/10.1021/acs.joc.4c01738
Publication status	Published - 20 Sept 2024

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title = "Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B",

abstract = "The racemic modification of the α-tropolone-containing sesquiterpene olaximbriside A [viz. (±)-4)] has been prepared over 12 steps from the readily accessible decalin derivative 12. The last two of these steps involve a fully regiocontrolled substitution reaction of bromotropone 24. The aromatization of a stereoisomeric and co-produced form of compound 12 has provided (±)-olaximbriside B [(±)-5)].",

author = "Qi Chen and Banwell, {Martin G.} and Gardiner, {Michael G.} and Ping Lan and Shen Tan",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

month = sep,

day = "20",

doi = "10.1021/acs.joc.4c01738",

language = "English",

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journal = "Journal of Organic Chemistry",

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T1 - Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B

AU - Chen, Qi

AU - Banwell, Martin G.

AU - Gardiner, Michael G.

AU - Lan, Ping

AU - Tan, Shen

PY - 2024/9/20

Y1 - 2024/9/20

N2 - The racemic modification of the α-tropolone-containing sesquiterpene olaximbriside A [viz. (±)-4)] has been prepared over 12 steps from the readily accessible decalin derivative 12. The last two of these steps involve a fully regiocontrolled substitution reaction of bromotropone 24. The aromatization of a stereoisomeric and co-produced form of compound 12 has provided (±)-olaximbriside B [(±)-5)].

AB - The racemic modification of the α-tropolone-containing sesquiterpene olaximbriside A [viz. (±)-4)] has been prepared over 12 steps from the readily accessible decalin derivative 12. The last two of these steps involve a fully regiocontrolled substitution reaction of bromotropone 24. The aromatization of a stereoisomeric and co-produced form of compound 12 has provided (±)-olaximbriside B [(±)-5)].

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U2 - 10.1021/acs.joc.4c01738

DO - 10.1021/acs.joc.4c01738

M3 - Article

AN - SCOPUS:85203817142

SN - 0022-3263

VL - 89

SP - 13530

EP - 13539

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

Total Syntheses of the Tropolone-Containing Sesquiterpene Olaximbriside A and Its Decarbonylated Counterpart Olaximbriside B

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