Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol

Fabrice Gallou; David W.C. MacMillan; Larry E. Overman; Leo A. Paquette; Lewis D. Pennington; Jiong Yang

doi:10.1021/ol000345m

Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol

Fabrice Gallou, David W.C. MacMillan, Larry E. Overman, Leo A. Paquette, Lewis D. Pennington, Jiong Yang

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

58 Scopus citations

Abstract

(equation presented) Two distinctively different total syntheses of natural sclerophytin A in its revised structural formulation are reported. The first proceeds from (S)-carvone via a cladiellene triol and involves photoisomerization of the double bond. The second route makes use of (5S)-5-(d-menthyloxy)-2(5H)-furanone, which is subjected to cycloaddition, Claisen ring expansion, and regiocontrolled dihydroxylation tactics.

Original language	English (US)
Pages (from-to)	135-137
Number of pages	3
Journal	Organic letters
Volume	3
Issue number	1
DOIs	https://doi.org/10.1021/ol000345m
State	Published - Jan 11 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol000345m

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title = "Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol",

abstract = "(equation presented) Two distinctively different total syntheses of natural sclerophytin A in its revised structural formulation are reported. The first proceeds from (S)-carvone via a cladiellene triol and involves photoisomerization of the double bond. The second route makes use of (5S)-5-(d-menthyloxy)-2(5H)-furanone, which is subjected to cycloaddition, Claisen ring expansion, and regiocontrolled dihydroxylation tactics.",

author = "Fabrice Gallou and MacMillan, {David W.C.} and Overman, {Larry E.} and Paquette, {Leo A.} and Pennington, {Lewis D.} and Jiong Yang",

year = "2001",

month = jan,

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doi = "10.1021/ol000345m",

language = "English (US)",

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pages = "135--137",

journal = "Organic letters",

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T1 - Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol

AU - Gallou, Fabrice

AU - MacMillan, David W.C.

AU - Overman, Larry E.

AU - Paquette, Leo A.

AU - Pennington, Lewis D.

AU - Yang, Jiong

PY - 2001/1/11

Y1 - 2001/1/11

N2 - (equation presented) Two distinctively different total syntheses of natural sclerophytin A in its revised structural formulation are reported. The first proceeds from (S)-carvone via a cladiellene triol and involves photoisomerization of the double bond. The second route makes use of (5S)-5-(d-menthyloxy)-2(5H)-furanone, which is subjected to cycloaddition, Claisen ring expansion, and regiocontrolled dihydroxylation tactics.

AB - (equation presented) Two distinctively different total syntheses of natural sclerophytin A in its revised structural formulation are reported. The first proceeds from (S)-carvone via a cladiellene triol and involves photoisomerization of the double bond. The second route makes use of (5S)-5-(d-menthyloxy)-2(5H)-furanone, which is subjected to cycloaddition, Claisen ring expansion, and regiocontrolled dihydroxylation tactics.

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ER -

Enantioselective syntheses of authentic sclerophytin A, sclerophytin B, and cladiell-11-ene-3,6,7-triol

Abstract

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