Abstract:
:Steroidal C19-hydroxylation is pivotal to the synthesis of naturally occurring bioactive C19-OH steroids and 19-norsteroidal pharmaceuticals. However, realizing this transformation is proved to be challenging through either chemical or biological synthesis. Herein, we report a highly efficient method to synthesize 19-OH-cortexolone in 80% efficiency at the multi-gram scale. The obtained C19-OH-cortexolone can be readily transformed to various synthetically useful intermediates including the industrially valuable 19-OH-androstenedione, which can serve as a basis for synthesis of C19-functionalized steroids as well as 19-nor steroidal drugs. Using this biocatalytic C19-hydroxylation method, the unified synthesis of six C19-hydroxylated pregnanes is achieved in just 4 to 9 steps. In addition, the structure of sclerosteroid B is revised on the basis of our synthesis.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Wang J,Zhang Y,Liu H,Shang Y,Zhou L,Wei P,Yin WB,Deng Z,Qu X,Zhou Qdoi
10.1038/s41467-019-11344-0subject
Has Abstractpub_date
2019-07-29 00:00:00pages
3378issue
1issn
2041-1723pii
10.1038/s41467-019-11344-0journal_volume
10pub_type
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