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Synthesis of prostaglandin D1 and D2 via the three-component coupling process

✍ Scribed by M. Suzuki; A. Yanagisawa; R. Noyori

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
235 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

1384 OC, 21 h) was followed by reduction with excess tributyltin hydride-di-tert-butyl peroxide (50 "C, 7.5 h)" to give the deoxygenated, acetylenic ketone _ (85%. [ CLI i6 -46.1" (2 0.375. CH30H)). Subsequent stereoselective reduction with diisobutylaluminum hydride modified by 2, 6-di-tert-butyl-4-methylpheno17 ( 12 equiv, toluene, -78 to -20 OC for 2 h and then -20 "C for 1.7 h) gave the 9a alcohol 12 12 (86%, [ aI;6 -28.8" (5 1.30, CH30H)). The undesired 9Γ­3 isomer was formed in only 8% yield. Partial hydrogenation of the acetylenic bond over Lindlar catalyst in a benzene-cyclohexane-cyclohexene mixture (1 atm, 26 OC, 13 h) gave the suitably protected PGF20 derivative 2, [ aly -20.6O (2 1.02, CH30H), in 96% yield. Tetrahydropyranyl protection of the 9-hydroxyl group to give 15 (lOO%, 1 aI,, 27 -8.3 (c 0.92, CH30H)), desilylation _ with (n-C H ) 4 94 NF in THF (15 equiv, 26 OC, 3 h) giving 16 (95%, [ CX]~ -6.766 (5 0.72 CH30H)), and saponification (20% NaOH-H20, 16 OC, 18.3 h) followed by Jones oxidation of

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