C. F. Morrison et al. / Tetrahedron Letters 50 (2009) 7021–7023
7023
Acknowledgment
S
OHC
O
CH2(CH2SH)2,
ZnCl2, CH2Cl2
S
We thank the Natural Sciences and Engineering Research Coun-
cil of Canada for financial support.
O
OMe
100%
OMe
OEt OMe
OEt OMe
21
Supplementary data
24
Experimental procedures and characterization data for com-
pounds 1, 7, 8, 10–12, 14–17, 19a–d, 20, 24–28 are available. Sup-
plementary data associated with this article can be found, in the
TBSO
S
H
S
H
OMe
O
References and notes
OH OMe
25 (62%)
LDA, THF,
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−
1. LDA, THF, 78 °C
24
−
78 °C to rt
100%
+
6
2.
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TBSO
H
S
S
H
O
OMe
O
OMe
OEt
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Scheme 3.
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OMe
OMe
S
1. LDA, THF, −78 °C
S
H
O
H
24
H
OH
AcO
AcO
= 27
2.
O
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28
−
84%
THF, 78°C to rt
Scheme 4.
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a
,b-unsaturated system. We anticipate that dithiane-ester cycliza-
tions may be useful for the synthesis of analogues of antibiotics
such as 2.20