(–)-Procyanidin C2 (TKGP-130126) K. Ohmori, K.

Suzuki1), 2)

OH

HO O
OH

OH OH
HO
HO O
OH

OH OH
HO
HO O
OH

OH
HO

Activity Antitumor（抗腫瘍活性）, Hair growth（育毛作用）

(A) regioselective bromination, (B) NIS-promoted Friedel–Crafts reaction,

Key Reactions
(C) Lewis acid-promoted Friedel–Crafts reaction
OBn

BnO O
OBn
OH 1) ?, pyridine OBn
2) ?, H2O Br OBn
HO O BnCl, DMF BnO O BnO OAc
OH OBn
3) ?, AcOH ?, CH2Cl2
OH 4) NBS OBn
HO 5) PhSH, ? BnO SPh
B-063 B-037
(A) (B)

OBn
Br
OBn BnO O
OBn OBn
Br BnO O
OBn
BnO O OBn
OBn OBn
OBn BnO
BnO BnO O
OBn OBn OBn
BnO ?, CH2Cl2
BnO O OBn
OBn OBn
BnO
OBn (C) BnO O
OBn
BnO OAc
OBn
BnO

1) ?, THF
(–)-Procyanidin C2
2) H2, Pd(OH)2

References:
1) K. Ohmori, N. Ushimaru, K. Suzuki, Proc. Natl. Acad. Sci., U.S.A., 101, 12002 (2004)
2) K. Ohmori, N. Ushimaru, K. Suzuki, Tetrahedron Lett., 43, 7753 (2002)