NDLI: Studies towards the synthesis of the functionalized C3–C14 decalin framework of alchivemycin A

Content Provider	Semantic Scholar
Author	Ma, Kaiqing Liao, Daohong Yang, Shaoqiang Li, Xiaofei Lei, Xiaoguang
Copyright Year	2016
Abstract	We report our synthetic studies towards the synthesis of the C3–C14 fragment of alchivemycin A. The synthesis featured an asymmetric alkylation with excellent diastereoselectivity and a one-pot Julia–Kocienski olefination with excellent E-selectivity. An intramolecular Diels–Alder reaction was employed to construct the highly functionalized cis-decalin framework. Interestingly, the stereochemical outcome was not expected to generate the two stereoisomers 20 and 21 instead of the desired cis-decalin 5. The detailed mechanism of this transformation was discussed. These synthetic endeavors have offered us a number of crucial insights for the synthesis of the complex natural product alchivemycin A.
Starting Page	251
Ending Page	258
Page Count	8
File Format	PDF HTM / HTML
DOI	10.1039/C5QO00343A
Alternate Webpage(s)	http://www.rsc.org/suppdata/c5/qo/c5qo00343a/c5qo00343a1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/C5QO00343A
Volume Number	3
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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