(–)-Lagunamycin (120721-TKGP) K. Tatsuta, S.

Hosokawa1)

Me Me

Me

Me
O
N
Me N

O N O
H
O

Activity Inhibition of 5-lipoxygenase（5-リポキシゲナーゼ阻害活性）

(A) vinylogous Mukaiyama aldol reaction, (B) Nicolaou oxidation,

Key Reactions
(C) Knorr condensation

Me Me
?, Et3N
Me ? NaHMDS Me CHO
Me
OH
Me i-Pr N O N O
Me TBSCl Me ?, CH2Cl2
O THF
HN O O O TBSO O
–78 °C (A)
O

LHMDS
Me Me Me PhSO2Cl Me Me Me ? Me Me Me
N O N O
Me THF Me THF Me
OH O O OSO2Ph O O OH

OMe

? Me Me Me Me
? Me Me Me ? H2N OH
Me COOH
hexane Me CHO THF
OH EDCI·HCl
CH2Cl2
 Me Me Me Me Me Me
C-40
Me Me Me

Me ? Me aq H2SO4 Me
OMe OMe O
Me toluene-DMSO Me MeCN, rt; Me
OH O O
rt to 40 °C
O O O
N OH (B) N O N OH
H H H
O O

Me Me

Me

Na2S2O4 Me ?
? OH
40 °C; (C) Me

O N OH
H
OH

Me Me Me Me

Me Me
?
Me DBU Me
O O
N
Me THF Me N

O N OH O N O
H B-55 H
O O
(–)-Lagunamycin

Reference:
1) S. Hosokawa, S. Kuroda, K. Imamura, K. Tatsuta, Tetrahedron Lett., 47, 6183 (2006)