Model Study of Maoecrystal

In 2009, Danishefsky s group reported the model study of Maoecrystal V (Fig. 1.21) [32]. The key reactions in their study mainly include Pd(II)-catalyzed coupling reaction [2, 3] rearrangement reaction and intramolecular Diels-Alder reaction. It worth mentioning that the three research groups mentioned above used the similar synthetic strategy to complete the synthesis of core structure model of Maoecrystal V. 

In this chapter, we completed the model study of Maoecrystal V. The synthesis route is shown briefly in Fig. 2.30. 

In model study of Maoecrystal V, the skeleton of the natural product was successfully established, and three contiguous chiral centers, C8, C9, CIO, were also built. Based on the information supplied by model research, the total synthesis of Maoecrystal V was developed. The retro-synthetic analysis is shown in Fig. 3.1. 

The total synthesis of natural product Maoecrystal V was completed by an efficient convergent strategy. In the model study of Maoecrystal V, Wessly oxidative dearomatization and IMDA reaction were considered as the key reactions to rapidly construct the tetracyclic structure of Maoecrystal V, which established the foundation for total synthesis of Maoecrystal V. Through an eight-step route with a total yield of 20 %, the model study was completed with high efficiency. 

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