Application of palladium-catalyzed [3+ 2] cycloaddition technology to the elaboration of kempane diterpenes. Stereocontrolled synthesis of (.+-.)-3. alpha.-hydroxy-7. …

…, MA Kinsella, CM Blackwell, LG Anderson

Index: Paquette, Leo A.; Sauer, Daryl R.; Cleary, Darryl G.; Kinsella, Mary A.; Blackwell, Christopher M.; Anderson, Lawrence G. Journal of the American Chemical Society, 1992 , vol. 114, # 19 p. 7375 - 7387

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Citation Number: 57

Abstract

Abstract: The total synthesis of three hydroxykempenones (8-10) has been accomplished. The retrosynthetic elements of the strategy focused on setting four key stereocenters in rings A and B, followed by annulation of ring C and ultimate cyclization to construct the seven- membered ring, D. Since the target molecule camw eight contiguous stereogenic centers, proper attention to stereocontrolled processes was mandatory. The key features of the ...