Formation of the C6–N–C20 Bridge for Entry into the Hetisane Skeleton

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Contents Vol 61(3)

doi:10.1071/CH07428

Formation of the C6–N–C20 Bridge for Entry into the Hetisane Skeleton

Oliver E. Hutt ^A ^B, Lewis N. Mander ^A

^A Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia.
^B Corresponding author. Email: huttx005@umn.edu





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Australian Journal of Chemistry 61(3) 204–208 http://dx.doi.org/10.1071/CH07428
Submitted: 13 December 2007 Accepted: 5 March 2008 Published online: 26 March 2008

Abstract

As a result of recent investigations into the total synthesis of the complex diterpene alkaloid nominine, the preparation of two new heterocyclic intermediates is now described. The cyclic ether 10 was derived from an intramolecular Mitsunobu reaction. The precursor hydroxylated compound 9 was the minor product of the hydroboration of alkene 7, which proceeded with an unexpected stereochemical outcome. The lactam 3 was derived from the hydrogenation of oxime 18 through presumed cyclization of the amino ester.