182156-02-1Relevant articles and documents
Evaluation of furan photooxygenation as a device for construction of the zaragozic acid (squalestatin) core
Maezaki, Naoyoshi,Gijsen, Harrie J. M.,Sun, Li-Qiang,Paquette, Leo A.
, p. 6685 - 6692 (2007/10/03)
A practical application of the photooxygenation chemistry of 3-substituted furans to construction of the zaragozic acid/squalestatin backbone is described. Although addition of 3-lithiofuran to the tartrate-derived aldehyde 7 proceeds without chelation control to give a 1:1 mixture of diastereomeric alcohols 8, it is demonstrated initially that ready conversion to the polyfunctional intermediate 16 is possible by sequential treatment of 9 with singlet oxygen, sodium borohydride, and triisopropylsilyl triflate. The actual enantiocontrolled route consisted of oxidation of 8 to the ketone and Wittig olefination of the latter in advance of asymmetric dihydroxylation with AD-mix-β. Cnce this series of transformations had been accomplished, formation of the target product 30 was realized by an entirely comparable photooxygenation.