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0041982462
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Alcohol 6 is available from D-glyceraldehyde acetonide via a stereoselective addition of 1-(trimethylsilyl)vinyl copper, followed by protodesilylation. See: (a) Sato, F.; Kusakabe, M. Chem. Lett. 1986, 1473.
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equation presented
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84982344292
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Preparation of stannane 10 is conveniently carried out via deprotonation of 3-methyl-3-buten-1-ol with 2 equiv of Schlosser's base (KOtBu/ "BuLi in hexanes) (see (a) Schlosser, M.; Hartmann, J. Angew. Chem., Int. Ed. Engl. 1973, 12, 508.
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0041982453
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(b) Collum, D. B.; Mguirk, P. R. J. Org. Chem. 1989, 49, 843.) and quenching the resulting dianion with tributyltin iodide. Protection of the resulting primary alcohol with trimethylacetyl chloride/ pyridine provided stannane 10.
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Collum, D.B.1
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0032192220
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For more examples of asymmetric allylations being used for the synthesis of complex homoallylic alcohols, see: Williams, D. R.; Brooks, J D. A.; Meyer, K. G.; Clark, M. P. Tetrahedron Lett. 1998, 39, 7251.
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0042483157
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37
-
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85087226461
-
-
note
-
2 (92%);
-
-
-
-
38
-
-
85087225916
-
-
3, DBU (81%);
-
3, DBU (81%);
-
-
-
-
39
-
-
85087228668
-
-
2 (85%). (equation presented)
-
2 (85%). (equation presented)
-
-
-
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41
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0028061479
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(b) Kinishima, M.; Hioki, K.; Kono, K.; Sakuma, T.; Tani, S. Chem. Pharm. Bull. 1994, 42, 2190.
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-
42
-
-
0042984009
-
-
note
-
The oxalyl chloride Swern procedure (see ref 12) gave a side product resulting from dichlorination at the C(32) position (72% yield).
-
-
-
-
43
-
-
85087228411
-
-
note
-
2 (91% yield).
-
-
-
-
44
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-
0009569128
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Guindon, Y.; Fortin, R.; Yoakim, C.; Gillard, J. W. Tetrahedron Lett. 1984, 25, 4717.
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-
-
0041982457
-
-
note
-
Additionally, small quantities of tetraene 20 have been observed in the Julia olefination reaction resulting from subsequent elimination of methanol. (equation presented)
-
-
-
-
49
-
-
0042483164
-
-
note
-
For example, reaction of sulfone 4 with cinnamaldehyde resulted in an 8:1 ratio of (E,E) to (E,Z) dienes. (equation presented)
-
-
-
-
50
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-
0001700380
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Roelofs, W.; Comeau, A.; Hill, A.; Milicevic, G. Science 1971, 174, 297.
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