An Economical and Practical Synthesis of rac‐(Z)‐β‐Santalol: Application of a Scriabine‐Inspired Reaction to Alkenes Results in the One‐Step Preparation of a Key Intermediate1. Issue 34 (29th October 2014)

• Record Type: Journal Article
• Authors: Birkbeck, Anthony A.; Marquet, Xavier; Millet, Pascal; Pamingle, Hervé
• Is Part Of: European journal of organic chemistry. Issue 34(2014)
• Page Start: 7582
• Page End: 7585
• Publication Date: 2014-10-29
• Subjects: Total synthesis -- Terpenoids -- Fragrances -- Alkenes -- Enols -- Ene reaction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403219
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An economical and practical synthesis of rac ‐( Z )‐β‐santalol was accomplished. The key coupling step is based on a Scriabine‐inspired reaction of a dienyl diacetate substrate and an alkene. The total synthesis was achieved in five steps (longest linear sequence) in 19 % overall yield from cyclopentadiene. Abstract : An economical and scalable synthesis of rac ‐( Z )‐β‐santalol is accomplished. The key coupling step is based on a Scriabine‐inspired reaction of a dienyl diacetate substrate and an alkene. The total synthesis is achieved in five steps (longest linear sequence) in 19 % overall yield from cyclopentadiene; Cp* = C5 Me5, cod = 1, 5‐cyclooctadiene, Tf = trifluoromethylsulfonyl.