gem-Dibromocyclopropanes and enzymatically derived cis-1,2-dihydrocatechols as building blocks in alkaloid synthesis

Banwell, Martin G.; Gao, Nadia Yuqian; Ma, Xinghua; Petit, Laurent; White, Lorenzo V.; Schwartz, Brett D.; Willis, Anthony C.; Cade, Ian A.

doi:10.1351/pac-con-11-07-05

Cited by 15 publications

(2 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Finally, the pronounced achievements of the Australian group, led by Banwell, ,,− in the synthesis of chiral, nonracemic Amaryllidaceae alkaloids, although based only on chemoenzymatically prepared starting material, that is, the cis -1,2-dihydrocatechols of general formula 986 , deserves attention (Chart ). Applying enantiomerically pure diols of type 986 , readily available from the corresponding aromatics by chemoenzymatic transformations, was reviewed by Hudlicky .…”

Section: Biocatalytic Route To Isoquinoline Alkaloidsmentioning

confidence: 99%

“…Applying enantiomerically pure diols of type 986 , readily available from the corresponding aromatics by chemoenzymatic transformations, was reviewed by Hudlicky . A diversity of alkaloid’s structures have been constructed, e.g., of lycorine-, ,, crynine-, , montanine-, ,, as well as of pancratistatine-type natural and unnatural products.…”

Section: Biocatalytic Route To Isoquinoline Alkaloidsmentioning

confidence: 99%

See 1 more Smart Citation

Asymmetric Synthesis of Isoquinoline Alkaloids: 2004–2015

2016

View full text Add to dashboard Cite

In the past decade, the asymmetric synthesis of chiral nonracemic isoquinoline alkaloids, a family of natural products showing a wide range of structural diversity and biological and pharmaceutical activity, has been based either on continuation or improvement of known traditional methods or on new, recently developed, strategies. Both diastereoselective and enantioselective catalytic methods have been applied. This review describes the stereochemically modified traditional syntheses (the Pictet-Spengler, the Bischler-Napieralski, and the Pomeranz-Fritsch-Bobbitt) along with strategies based on closing of the nitrogen-containing ring B of the isoquinoline core by the formation of bonds between C-N, N-C, C-N/N-C, and C-N/C-C atoms. Methods involving introduction of substituents at the C1 carbon of isoquinoline core along with syntheses applying various biocatalytic techniques have also been reviewed.

show abstract