A Synthesis of (–)‐(R)‐ and (+)‐(S)‐Lavandulol, (+)‐Lavandulyl 2‐Methylbutanoate, and (+)‐Lavandulyl Senecioate through Ortho­ester Johnson–Claisen Rearrangement. Issue 23 (25th June 2013)

• Record Type: Journal Article
• Authors: Fernandes, Rodney A.; Chowdhury, Asim K.
• Is Part Of: European journal of organic chemistry. Issue 23(2013)
• Page Start: 5165
• Page End: 5170
• Publication Date: 2013-06-25
• Subjects: Natural products -- Total synthesis -- Rearrangement -- Terpenoids -- Pheromones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300520
• Languages: English
• ISSNs: 1434-193X

Abstract

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