Total synthesis of (+)-aureol

Kevin K.W. Kuan; Henry P. Pepper; Witold M. Bloch; Jonathan H. George

doi:10.1021/ol301715u

Total synthesis of (+)-aureol

Kevin K.W. Kuan, Henry P. Pepper, Witold M. Bloch, Jonathan H. George

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

36 Citations (Scopus)

Abstract

A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimetic cycloetherification reaction.

Original language	English
Pages (from-to)	4710-4713
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	18
DOIs	https://doi.org/10.1021/ol301715u
Publication status	Published or Issued - 21 Sept 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol301715u

Cite this

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title = "Total synthesis of (+)-aureol",

abstract = "A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimetic cycloetherification reaction.",

author = "Kuan, {Kevin K.W.} and Pepper, {Henry P.} and Bloch, {Witold M.} and George, {Jonathan H.}",

year = "2012",

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AU - Pepper, Henry P.

AU - Bloch, Witold M.

AU - George, Jonathan H.

PY - 2012/9/21

Y1 - 2012/9/21

N2 - A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimetic cycloetherification reaction.

AB - A total synthesis of the marine sponge meroterpenoid (+)-aureol has been achieved in 12 steps (6% overall yield) from (+)-sclareolide. Key steps of the synthesis include a biosynthetically inspired sequence of 1,2-hydride and methyl shifts, and a biomimetic cycloetherification reaction.

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VL - 14

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JO - Organic Letters

JF - Organic Letters

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ER -

Total synthesis of (+)-aureol

Abstract

ASJC Scopus subject areas

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