A convergent route for the total synthesis of malyngamides O, P, Q, and R.
A convergent, enantioselective and general synthetic route to a class of marine natural products-malyngamides O (1), P (2), Q (3), R (4), 5''-epi-3 and 5''-epi-4-bearing a novel vinyl chloride structural motif was developed. The key steps involved construction of the vinyl chloride functionality by Wittig reaction, a DCC/HOBt-promoted amidation, an aldol reaction in the construction of the basic backbone of 1, 2, 3, 4, 5''-epi-3, and 5''-epi-4, and methylation of an enol moiety via either base/acid conditions or a Mitsunobu reaction. Moreover, the absolute configuration of the stereogenic center at C-5'' in 3 was further confirmed by synthesis of the natural product and its C-5'' epimer.
Chen
Jie
J
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China.
Fu
Xiao-Gang
XG
Zhou
Ling
L
Zhang
Jun-Tao
JT
Qi
Xian-Liang
XL
Cao
Xiao-Ping
XP
D000144:Acids, Acyclic / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles; D013237:Stereoisomerism; D014752:Vinyl Chloride
D000144:Acids, Acyclic; D000475:Alkenes; D000577:Amides; D001688:Biological Products; D011758:Pyrroles; C416568:malyngamide O; C416569:malyngamide P; C413034:malyngamide Q; C413035:malyngamide R; D014752:Vinyl Chloride