Studies directed toward the first total synthesis of acremodiol and acremonol

A concise stereoselective total synthesis of diplodialide C

“…The target molecule 3 could be synthesized through Yamaguchi's macrolactonization of a hydroxyl acid 5 which in turn could be obtained from olefins 6 and 7 [14]. The olefin 6 could be prepared from commercially available homoallylic alcohol (8) by simple chemical transformations.…”

“…Regioselective opening of the chiral epoxide 10, upon reaction with vinylmagnesium bromide in dry ether in the presence of CuI [9,10] gave alcohol 11 (88 %), which upon subsequent treatment with TBDPSCl and imidazole in CH 2 Cl 2 gave silyl ether 6 in 90 % yield. Further, silyl ether 6 was subjected to crossmetathesis [11][12][13] with known olefin 7 [14] in the presence of 10 mol% Grubbs second-generation catalyst in CH 2 Cl 2 , at reflux afforded cross-metathesis product 12 (E/Z 90:10) in 57 % yield, along with 12a in 21 % yield, a homodimer of 7. The simultaneous reduction of olefin and deprotection of the benzyl group with Pd/C in EtOAc yielded saturated alcohol 13 in 91 % yield.…”

Synthesis of (-)-Pyrenophorol

“…We finally discovered that 14 can be cleanly debenzylated when treated with TiCl 4 in CH 2 Cl 2 (Scheme 3). 12 Finally, tetrahydropyrenophorol was also prepared by reducing the double bond. The spectroscopic data of our (-)-pyrenophorol (1) and tetrahydropyrenophorol (5) are identical to those reported in the literature.…”

An Alternative Total Synthesis of (–)-Pyrenophorol

“…In continuation of our interest on the synthesis of macrodiolides [16][17][18][19] herein, we report the synthesis of pyrenophorol (1) by adopting dimerization of hydroxy acid using Mitsunobu protocol.…”