A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-Methylbutanoate, and (+)-Lavandulyl Senecioate through Orthoester Johnson-Claisen Rearrangement

被引：10

作者：

Fernandes, Rodney A. ^{[1
]}

Chowdhury, Asim K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 23期

关键词：

Natural products; Total synthesis; Rearrangement; Terpenoids; Pheromones; PINK HIBISCUS MEALYBUG; SEX-PHEROMONE; ENANTIOSELECTIVE SYNTHESIS; AGGREGATION PHEROMONE; RACEMIC LAVANDULOL; PLANOCOCCUS-FICUS; ALLYLIC ALCOHOLS; VINE MEALYBUG; ACID; (R)-LAVANDULOL;

D O I：

10.1002/ejoc.201300520

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented in this paper. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step.

引用

页码：5165 / 5170

页数：6

共 14 条

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[3] Total synthesis of (-)-2-oxo epimesembranol and (+)-dihydromaritidine via a key Johnson-Claisen rearrangement
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[4] THE JOHNSON-CLAISEN REARRANGEMENT OF 5-HYDROXY-2-METHYLENEALKANENITRILES - STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED TRISUBSTITUTED ALKENES
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TETRAHEDRON LETTERS, 1995, 36 (05) : 757 - 758
[5] Control of Diastereoselectivity in Orthoester Johnson-Claisen Rearrangement of Tartrate-Based Allyl Alcohol: An Efficient Synthesis of Arundic Acid, a Potential Therapeutic Agent for Alzheimer's Disease
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Ingle, Arun B.
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[6] An Efficient Total Synthesis of (-)-(R), (+)-(S)-Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α-Aminooxylation and [3,3] Claisen Rearrangement
Bhosale, Viraj A.
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CHEMISTRYSELECT, 2017, 2 (03): : 1262 - 1266
[7] Synthesis of β,γ-disubstituted-γ-lactones through a Johnson-Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
Fernandes, Rodney A.
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TETRAHEDRON-ASYMMETRY, 2009, 20 (24) : 2835 - 2844
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[9] ENANTIOSELECTIVE SYNTHESIS OF TRANS-OCTAHYDRO-1,6-DIOXONINDEN-4-YLPROPIONIC ACID FROM (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE BY TANDEM ORTHOESTER CLAISEN REARRANGEMENT
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TETRAHEDRON-ASYMMETRY, 2003, 14 (16) : 2401 - 2406

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