From D-camphor to the taxanes. Highly concise rearrangement-based approaches to taxusin and taxol

Many trees and shrubs of the Taxus family elaborate a fascinating collectio n of structurally complex polycyclic diterpenoids, the synthesis of which p rovides a valuable forum for assessing state-of-the-art methodology. Taxusi n and taxol have received the greatest revel of interest. From among the ma ny researchers inspired to explore the laboratory preparation of these targ ets, several have succeeded admirably. However, the approaches have most of ten been very lengthy. The goal of our research effort has been to implemen t a strategy generic to both molecules. The anticipation was that two centr al structural rearrangements, each with its own nuances of tailored design, would expedite construction of their common carbocyclic framework and perm it notably concise enantiocontrolled access from D-camphor as the key build ing block. The successes that have been realized during this investigation are summarized herein.