96443-55-9

Upstream product

• 164025-54-1 tert-butyl-(5-iodo-pentyloxy)-diphenyl-silane 
• 1341155-55-2 tert-butyl(((4S,5S)-5-((R)-6-(tert-butyldimethylsilyloxy)-heptyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)dimethylsilane 
• 1341155-22-3 ((4S,5S)-5-((R)-6-(tert-butyldimethylsilyloxy)heptyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol 
• 1341155-26-7 ethyl (Z)-3-((4S,5S)-5-((R)-6-(tert-butyldimethylsilyloxy)heptyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 1341155-78-9 (Z)-3-((4S,5S)-5-((R)-6-(tert-butyldimethylsilyloxy)heptyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylic acid 
• 156647-91-5 (R)-(-)-8-Nonin-2-ol 
• 156715-27-4 (R)-(-)-4-Nonin-2-ol 
• 693-02-7 hex-1-yne 
• 912365-56-1 (R)-4-Benzyl-3-[(2R,3S,9S)-9-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-(4-methoxy-benzyloxy)-decanoyl]-oxazolidin-2-one 
• 1002728-60-0 (S)-non-8-en-2-ol 
• 1144482-80-3 (S)-7-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)heptan-2-ol 
• 1144482-74-5 C₁₄H₃₀O₂Si 

Downstream Products

• 1124292-29-0 (5R,6R,12R,Z)-5,6-dihydroxy-12-methyloxacyclododec-3-en-2-one 
• 851515-15-6 (E)-(-)-cladospolide B 
• 851616-13-2 cladospolide B 

Relevant academic research and scientific papers

A chemoenzymatic total synthesis of the undecenolide (-)-cladospolide C

The (-)-enantiomer, ent-3, of the natural product (+)-cladospolide C (3) has been prepared for the first time using the monochiral cis-1,2- dihydrocatechol 5 as starting material. Key steps include coupling of the derived acid 6 with the enzymatically gen

Synthesis of (+)-Cladospolide C

(+)-Cladospolide C was synthesized in eight steps with 5% total yield, using methyl acrylate, (3R,4R)-1,5-hexadiene-3,4-diol, and (6R)-6-hepten-2-ol as the starting materials. Two cross-metathesis reactions and Yamaguchi esterification were applied to assemble the three units into (+)-Cladospolide C. Unsuccessful routes using ring-closing metathesis are also discussed.

Enantioselective total synthesis of iso-cladospolide B, cladospolide C and cladospolide B from tartaric acid

The enantioselective synthesis of the natural products cladospolide B, cladospolide C, and iso-cladospolide B has been accomplished from tartaric acid. Key reactions in the synthetic sequence include the elaboration of a γ-hydroxy amide derived from tartaric acid via alkene cross metathesis, Yamaguchi lactonization, and ring closing metathesis.

Alkyne-mediated approach for total syntheses of cladospolides A, B, C and iso-cladospolide B

A general strategy for the stereoselective total syntheses of cladospolides A, B, and C and iso-cladospolide B has been accomplished. The key steps provide easy access to the target molecules and include an alkyne-zipper reaction, a Sharpless asymmetric e

Total synthesis of (+)-cladospolide A

A stereoselective total synthesis of (+)-cladospolide A from d-ribose is described. Key features of the synthesis include olefin cross metathesis and Yamaguchi lactonization. Georg Thieme Verlag Stuttgart New York.

A concise total synthesis of (+)-cladospolide D

A short and convergent total synthesis of (+)-cladospolide D is delineated, which involves olefin cross metathesis and furan oxidation to access the γ-oxo-α,β-unsaturated acid and Yamaguchi lactonization to construct the 12-membered ring as key steps. Copyright

A flexible and unified strategy for syntheses of cladospolides A, B, C, and iso-cladospolide B

A simple, efficient and flexible strategy for the syntheses of cladospolides A-C and iso-cladospolide B is reported here. This strategy involves Julia-Kocienski olefination and Yamaguchi macrolactonization as key steps, starting from either d-ribose or suitable tartaric acid esters. Although our initial efforts towards cladospolide A involving a ring closing metathetic approach were not successful, changing the mode of ring closure and the use of Julia-Kocienski olefination for the construction of the key intermediate solved this issue and paved the way for the completion of total syntheses of this class of natural products.

Stereoselective total synthesis of (-)-isocladospolide B and cladospolide B and C

The enantioselective synthesis of bioactive butenolides isocladospolide B, cladospolide B, and cladospolide-C has been achieved from (S)-propylene oxide. Of the three stereogenic centers, the C-4/C-5 vic-diol was obtained using diastereo- and enantio-selective Brown hydroxycrotylation, while the C-11 stereocenter was created by Jacobsen hydrolytic kinetic resolution. Georg Thieme Verlag Stuttgart · New York.

Stereoselective total synthesis of cladospolide A

A simple and highly efficient stereoselective total synthesis of cladospolide A, a polyketide natural product, has been achieved. The synthesis involves stereoselective zinc-mediated allylation, pivotal aldol coupling, and ring-closing metathesis. The pivotal aldol coupling is used for the first time for macrolide construction and provides an effective alternative to Yamaguchi macrolactonization. Georg Thieme Verlag Stuttgart · New York.

De novo asymmetric synthesis of cladospolide B-D: Structural reassignment of cladospolide D via the synthesis of its enantiomer

The enantioselective synthesis of cladospolide B, C, and (ent)-cladospolide D has been achieved in 11-15 steps from 1-nonyne. The route relies upon an alkyne zipper reaction to relay an ynone and dienoate functional groups across a nine carbon fragment, which enables a highly enantioselective Noyori ynone reduction and a diastereo-and regioselective Sharpless dihydroxylation of a dienoate. In addition to being a flexible approach to three members of the cladospolide natural products, this route for the first time correctly established the structure for cladospolide D.