The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol
2001 ◽
Vol 79
(11)
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pp. 1668-1680
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Keyword(s):
The total syntheses of the polyhydroxylated macrolactone (+)-aspicilin and a diastereoisomer have been achieved via a concise route, starting from the spatially desymmetrized (R',R',R,S)-2,3-butanediacetal-protected butane tetrol 13. The key steps include a regioselective silyl protection of 13 and a stereoselective Lewis acid mediated addition of allyltributylstannane to the equatorially disposed aldehyde of 4. Macrocyclization is achieved using ring closing metathesis, after which selective hydrogenation and protecting group removal yields the natural product.Key words: aspicilin, butanediacetal, desymmetrization, macrolactone, metathesis.
2017 ◽
Vol 15
(44)
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pp. 9408-9414
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Keyword(s):
Keyword(s):
2017 ◽
Vol 12
(9)
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pp. 1934578X1701200
2018 ◽
Vol 13
(7)
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pp. 1934578X1801300
Keyword(s):
2018 ◽
Vol 16
(4)
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pp. 585-592
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Keyword(s):
2016 ◽
Vol 14
(38)
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pp. 9072-9079
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2013 ◽
Vol 9
◽
pp. 1346-1351
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Keyword(s):