selected in order to give a broad range of substrate complexity and a variety of
substitution patterns (including, but not limited to, 2,6-cis and 2,6-trans THP rings)
[4–12]. These natural products have the added benefit of having been synthesized
many times using various strategies, which allows for direct comparison across the
different synthetic methods. This approach allowed for maximum utility within the
chapter using a relatively small subset of THP-containing natural products.
O
O
O
O
O
O
OH
HO
OH
O
O
CO 2 H
HO 2 C
OH
(+)-SCH 351448
O
O
O
O
OH
O
MeO 2 C
CO 2 Me
R
HO
OAc
OH
OH
A
B
Bryostatin 1 (R = OC(O)CH=CH-CH=CH-C 3 H 7 )
Bryostatin 11 (R = H)
C
O
N
O
O
O
O
R 1
R 2
N
O
O
MeO
HO
MeO
OH
Br
O
D
A
B
(+)-Phorboxazole A (R 1 = H, R 2 = OH)
(+)-Phorboxazole B (R 1 = OH, R 2 = H)
O
OMe O
O
O
O
O
O
N
NHCO 2 Me
O
OMe
O
R 1
OH OH
OH
O
OH
O
OR 2
O
MeO
O
OH
OH
OH
O
HO
O
OMe
A
B
A'
B'
Swinholide A (R 1 = R 2 = Me)
Swinholide B (R 1 = H, R 2 = Me)
Swinholide C (R 1 = Me, R 2 = H)
O
O
O
O
OAc
O
O
O
O
O
OH
OH
X
HO
AcO
OMe
HO
OH
OH
A
B
F
E
D
C
Spongistatin 1 (X = Cl)
Spongistatin 2 (X = H)
Leucascandrolide A
A
B
C
C
F
E
A
B
C
A'
B'
C'
Fig. 1 The representative natural products selected for this survey
Synthesis of Saturated Tetrahydropyrans
45