Asymmetric synthesis of the δ-lactone moiety in mevinic acid derivatives using an enzymatic procedure

8‐Oxabicyclo[3.2.1]oct‐6‐en‐3‐ones: Application to the Asymmetric Synthesis of Polyoxygenated Building Blocks

“…The lipase Candida cyclindracea (CCL) as well as Amano lipase AY‐30 gave monoacetate 52 in 80 % yield and 94–95 % ee . Enzymatic hydrolysis of the bisacetate derived from diol 51 was less efficient, and led to monoacetate 52 in only 54 % yield 43. Monoprotected diol 52 was transformed in three straightforward steps into lactone 53 , which corresponds to the lactone moiety of lovastatin and compactin, two potent inhibitors of HMG‐CoA reductase (see also Scheme for a nonenzymatic route).…”

A New, Non-Iterative Asymmetric Synthesis of Long-Chain 1,3-Polyols

“…The double adducts so-obtained are converted into meso-1,1-methylene-bis(4,6-dihydroxycyclohept-1-ene) derivatives that can be desymmetrised and transformed into pentadeca -1,3,5,7,9,11,13,15-octols and other long-chain polyketides with high stereo-and enantioselectivity. The method was inspired by the work of Lautens [5a] and Hoffmann and co-workers [5b] who have converted 8-oxabicyclo [3.2.1]oct-6-en-3-one into 7-carbon-1,3-polyols and analogues [5c] and by that of Kaku et al [6] who have transformed cyclohept-3-ene-1,6-diol into 1,3-polyols and their derivatives.…”

An Expeditious, Non‐Iterative, and Asymmetric Synthesis of 3,5,7,9,11,13,15‐Heptahydroxypentadecanals

“…[2] Inspired by the work of Lautens [3] and Hoffmann and co-workers, [4] who have converted 8-oxabicyclo [3.2.1]oct-6-en-3-one into seven-carbon chain 1,3-polyols and analogues, [5] and by that of Kaku et al, [6] who have transformed cyclohept-3-ene-1,6-diol into 1,3-polyols, we have proposed a new, non-iterative asymmetric synthesis of long-chain 1,3-polyols starting from the now readily available 2,2Ј-methylenebis(furan) (1). [7] This method involved a double [3ϩ4] cycloaddition between the 1,1,3-trichloro-2-oxyallyl cation and 1 (Scheme 1).…”