The total synthesis of (−)-aplysin via a lithiation–borylation–propenylation sequence

Content Provider	Semantic Scholar
Author	Fletcher, Catherine J. Blair, Daniel J. Wheelhouse, Katherine M. P. Aggarwal, Varinder K.
Copyright Year	2012
Abstract	Abstract A concise, highly enantioselective synthesis of sesquiterpene natural products (−)-debromoaplysin and (−)-aplysin has been completed. The key steps included lithiation–borylation of a secondary benzylic carbamate to give a tertiary boronic ester followed by propenylation which installed the quaternary stereocenter with complete enantioselectivity. Subsequent RCM followed by deprotection and in situ cyclization led to debromoaplysin with good diastereoselectivity from which the target compound was prepared in just eight overall steps.
Starting Page	7598
Ending Page	7604
Page Count	7
File Format	PDF HTM / HTML
DOI	10.1016/j.tet.2012.05.095
Volume Number	68
Alternate Webpage(s)	http://www.chm.bris.ac.uk/org/aggarwal/docs/publications/2012tetrahedron7598.pdf
Alternate Webpage(s)	https://doi.org/10.1016/j.tet.2012.05.095
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article