Isolation, structure and synthesis of maesanin, a host defense stimulant from an African medicinal platn maesa lanceolata

I Kubo, T Kamikawa, I Miura

Index: Kubo, Isao; Kamikawa, Tadao; Miura, Iwao Tetrahedron Letters, 1983 , vol. 24, # 36 p. 3825 - 3828

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Citation Number: 34

Abstract

[NMR (CCl 4 ) 0.92 (t, J=6 Hz, 3H), 2.34 (t, J=7 Hz, 2H), 5.24 (t, J=5 Hz, 2H), 9.59 (t, J=1.5 Hz, 1H)] was prepared from methylundecylenate by a four step sequence involving ozonization at −78°, Wittig olefination (n-pentylphosphonium iodide, n-BuLi, THF, −30° to room temp., 4 hrs), reduction (3.6 eq LiAlH 4 , Et 2 O, room temp, 2 hrs) and Swern oxidation [1.1 eq (COCl) 2 , 2.2 eq DMSO, CH 2 Cl 2 , −78°, 15 min then 5 eq Et 3 N] in 28% overall yield.