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OH
O
O
a, b
c, d, e
f
Cl
OCH
3
OCH
3
155
156
157
O
steps
OCH
3
(−)-3Z-Cembrene-A (
159
)
158
Reagents and Conditions: (a) LDA; (b) F
3
CSO
2
Cl; (c) (E)-1-lithio-2-methyl-1, 3-butadiene; (d) lithium
isopropenyl acetylide; (e) LAH; (f) KH, 18-crown-6, THF, rt.
Scheme 6-12
Br
OH
a
b
O
+
O
O
O
O
SO
2
Tol
162
160
161
SPh
SPh
c
d
OH
O
147
148
e
OH
(−)-
R
-Nephthenol (
40
)
(
−
)-
R
-Cembrene-A (
59
)
Reagents and Conditions: (a) i. H
2
, Pd/C; ii. (EtO)
2
POCH
2
CO
2
Bu-t; iii. DIBAL-H; iv. HPLC; v. PBr
3
;
(b) i. n-BuLi; ii. Na(Hg); iii. PBr
3,
PhSNa; iv. MsCl, K
2
CO
3
; (c) n-BuLi; (d) Na; (e) SOCl
2
,Py.
Scheme 6-13
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