Total Synthesis of (-)-Lamellodysidine A via an Intramolecular Diels-Alder Reaction.

  title={Total Synthesis of (-)-Lamellodysidine A via an Intramolecular Diels-Alder Reaction.},
  author={Shogo Kamo and Hitomi Kurosawa and Akinobu Matsuzawa and Kazuyuki Sugita},
  journal={Organic letters},
In this study, we achieved an eight-step enantioselective synthesis of (-)-lamellodysidine A, a structurally intriguing sesquiterpene natural product featuring a 5/5/6/6-fused tetracyclic skeleton that was obtained from the marine sponge Lamellodysidea herbacea. The key to the synthesis is a cascade reaction that includes an intramolecular Diels-Alder reaction. In addition, single-crystal X-ray crystallographic analysis of the synthetic (-)-lamellodysidine A clearly confirmed the proposed… 
1 Citations
Total Synthesis of (–)-Lamellodysidine A
  • Chemistry
  • 2022


Total synthesis of (+/-)-hedychilactone B: stepwise allenoate diene cycloaddition to prepare trimethyldecalin systems.
The exo adduct 4x, the major product of the stepwise cycloaddition of the diene 2 and the allenoate 3, has been converted into 1 via 7 steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether and an E-selective olefination.
Total Synthesis of Farnesin via an Excited-State Nazarov Reaction.
This is the first application of UV-light induced excited-state Nazarov cyclization of a non-aromatic dicyclicvinyl ketone in a total synthesis of farnesin through a convergent approach.
Enantioselective, Protecting-Group-Free Total Synthesis of Boscartin F.
The protecting-group-free total synthesis and stereochemical assignment of (-)-boscartin F have been reported and single-crystal X-ray crystallographic analysis of the semicarbazone derivative 22 confirmed the stereochemistry of boscart in F.
Total synthesis of phoslactomycin A.
A convergent total synthesis of the PP2A-inhibitor phoslactomycin A was achieved using a CuTC-mediated coupling of an alkenyl iodide C1-C13 fragment with an C14-C21 alkenyl stannane in the presence
Synthetic Approach Towards the Synthesis of Antimalarial Gomphostenin
An efficient and concise stereoselective synthesis towards the antimalarial (−)-Gomphostenin, starting with the enantiomerically pure Wieland–Miescher ketone, is reported. The key transformations of
Palladium-Catalyzed Cascade Assembly of Tricyclic Spiroethers from Diene-Alcohol Precursors.
This is the first attempt to link simple alcohols with diverse, medium-sized spiroether architectures and offers rapid delivery of a broad spectrum of tricyclic spiranoid ethers.
Stereoselective Synthesis of a Bicyclic Norsesquiterpene Backbone – A Possible Route to Nardosinane Derivatives
We have developed an efficient diastereoselective synthetic route towards a nardosinane sesquiterpene scaffold. The strategy used a key bicyclic diene intermediate 11a, and allowed access to valuable
Stereocontrolled total synthesis of polygalolide A.
The total synthesis of polygalolide A, a secondary metabolite that was isolated from a Chinese medicinal plant, is reported and it is revealed that the combination of trimethylsilyl trifluoromethanesulfonate and 2,4,6-collidine successfully afforded the desired product as a single diastereomer.