Total Synthesis of Sinensilactam A.

@article{Shao2018TotalSO,
  title={Total Synthesis of Sinensilactam A.},
  author={Wenbing Shao and Jun Huang and Kai Guo and Jianxian Gong and Zhen Yang},
  journal={Organic letters},
  year={2018},
  volume={20 7},
  pages={
          1857-1860
        }
}
The total synthesis of naturally occurring (±)-sinensilactam A was achieved in 18 steps. The key steps of this work are a rhodium-catalyzed [3 + 2] cycloaddition for construction of the two all-carbon vicinal quaternary centers and a convergent and tandem condensation of the in situ generated N-acyliminium intermediate with aldehyde 20. This enabled implementation of a unified strategy for stereoselective formation of the tetracyclic hemiaminal core of sinensilactam A in a later stage. The… 
17 Citations
A concise total synthesis of unprecedented tetranorsesquiterpenoids applanatumol Z5
Abstract A concise total synthesis of tetranorsesquiterpenoids applanatumol Z5 (3), possessing unique 6/5/5 ring system was disclosed with 7-step in 5-pot from commercially available starting
Protecting-Group-Free Total Syntheses of (±)-Norascyronones A and B.
TLDR
This investigation indicated that the C5 stereogenic center of norascyronone C plays a critical role in the proposed biomimetic oxidative reaction for B-ring formation.
Collective enantioselective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B and (-)-lingzhiol: divergent reactivity of styrene.
The collective total synthesis of (+)-sinensilactam A, (+)-lingzhilactone B, (+)-lingzhilactone C and (-)-lingzhiol has been accomplished from a common epoxide intermediate 9. Chemoselective epoxy
Concise synthesis of the core structure of madreporanone by Rh-catalyzed [3+2] cycloaddition
Abstract A model study toward total synthesis of madreporanone, a novel diterpene isolated from Azorella madreporica, was investigated. The [3.3.0] bicyclic core of madreporanone bearing a
Total synthesis of applanatumols X and Y
Abstract The first total synthesis of applanatumols X and Y, isolated from Ganoderma applanatum, have been accomplished in 9 and 10 steps, respectively, using the key intermediate in the synthesis of
Asymmetric Total Synthesis of (+)-Waihoensene.
TLDR
Control experiments and density functional theory calculations support the proposed HAT process.
All-carbon [3 + 2] cycloaddition in natural product synthesis
TLDR
The development of all-carbon [3 + 2] cycloadditions is presented and their application in natural product synthesis reported in the last decade covering 2011–2020 (inclusive).
Regio- and Diastereoselective Copper-Catalyzed Carbomagnesiation for the Synthesis of Penta- and Hexa-Substituted Cyclopropanes.
Despite the highly strained nature of cyclopropanes possessing three vicinal quaternary carbon stereocenters, the regio- and diastereoselective copper-catalyzed carbomagnesiation reaction of
Scalable Synthesis of Vicinal Quaternary Stereocenters via the Solid-State Photodecarbonylation of a Crystalline Hexasubstituted Ketone.
TLDR
This work reports the synthesis and stereospecific solid-state photodecarbonylation of a hexasubstituted ketone featuring six distinct α-substituents including vicinal all-carbon quaternary stereocenters and the potential of this transformation toward constructing complex architectures.
Retro-metal-ene versus retro-Aldol: mechanistic insight into Rh-catalysed formal [3+2] cycloaddition.
TLDR
A new C-C bond cleavage mechanism, retro-Aldol-type, is proposed and verified for this Rh-catalysed [3+2] cycloaddition reaction.
...
1
2
...