[Reaction: see text] A Dötz reaction employing a terminal alkyne and a Fischer-type alkenylchromium carbenoid led to a pentasubstituted benzene from which a major portion of the Streptomyces metabolite (-)-kendomycin was synthesized.

Construction of the C(1)–C(25) southern fragments of both spirastrellolide A and B are described. Highlights of the syntheses include effective use of the three component anion relay chemistry (ARC) tactic recently introduced by our laboratory, a stereoselective spirocyclization via concomitant Ferrier reaction to elaborate the BC spiroketal and use of two dithiane unions to install the A ring as well as C(22)–C(25) fragment. The synthesis proceeded with longest linear sequences of 33 and 32 steps respectively for spirastrellolide A and spirastrellolide B.

No abstract

No abstract