AI Article Synopsis
- The research presents a method combining the Mitsunobu reaction and a specific rearrangement of allylic azides, utilizing a chiral auxiliary system that effectively directs the formation of a preferred regioisomer due to its steric properties.
- This method can be followed by oxidative cleavage of the auxiliary or a ring-closing metathesis to create carbohydrate or heterocycles, while also allowing the chiral auxiliary to be reused.
- The methodology's practical applications are demonstrated through the total synthesis of compounds such as (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C.
Article Abstract
We describe a tandem Mitsunobu/3,3-sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carbo- or heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported.
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| http://dx.doi.org/10.1021/jo800817p | DOI Listing |
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