77663-54-8

Usage

InChI:InChI=1/C12H20O4/c1-9-5-3-2-4-6-10(13)11(14)7-8-12(15)16-9/h7-11,13-14H,2-6H2,1H3/b8-7-/t9-,10+,11-/m1/s1

Upstream product

• 426206-64-6 (3E,5R,6S,12R)-5,6-bis{[(1,1-dimethylethyl)dimethylsilyl]oxy}-12-methyloxacyclododec-3-en-2-one 
• 1197216-62-8 (R)-5-((4S,5S)-5-((R)-6-(tert-butyldimethylsilyloxy)heptyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane 
• 1197216-65-1 5-(3-((4S,5S)-2,2-dimethyl-5-((R)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-1,3-dioxolan-4-yl)propylsulfonyl)-1-phenyl-1H-tetrazole 
• 1197216-66-2 (R)-1-((4R,5S)-5-((R)-6-(tert-butyldimethylsilyloxy)heptyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 1197216-67-3 ethyl (E)-3-((4R,5S)-5-((R)-6-(tert-butyldimethylsilyloxy)heptyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 1197216-64-0 5-(3-((4S,5S)-2,2-dimethyl-5-((R)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-1,3-dioxolan-4-yl)propylthio)-1-phenyl-1H-tetrazole 
• 1197216-57-1 ethyl 3-((4S,5S)-2,2-dimethyl-5-((R)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-1,3-dioxolan-4-yl)propanoate 
• 1197216-58-2 3-((4S,5S)-2,2-dimethyl-5-((R)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-1,3-dioxolan-4-yl)propan-1-ol 
• 1197216-59-3 (R)-5-((4S,5S)-5-(but-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane 
• 1335001-92-7 ethyl (Z)-3-((4S,5S)-2,2-dimethyl-5-((R)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-1,3-dioxolan-4-yl)acrylate 
• 1197216-60-6 (R)-5-((4S,5S)-5-((R,E)-6-(tert-butyldimethylsilyloxy)hept-3-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane 
• 693-02-7 hex-1-yne 
• 156715-27-4 (R)-(-)-4-Nonin-2-ol 

Relevant academic research and scientific papers

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

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 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.

An expedient total synthesis of (-)-cladospolide A

A simple and efficient total synthesis of (-)-cladospolide A is described here, which involves either olefin cross metathesis or Julia-Kocienski olefination and Yamaguchi macrolactonization as key steps.

A chemoenzymatic total synthesis of the phytotoxic undecenolide (-)-cladospolide A.

An eleven-step synthesis of the title compound (1) from biocatalytically-derived and enantiomerically pure 'building blocks' alcohol (R)-(-)-9 and ester 13 is described. Attempts to construct the twelve-membered lactone ring of cladospolide A in a direct manner by using a ring-closing metathesis (RCM) reaction failed. However, a ten-membered lactone 19, could be constructed by such means and this was then subject to a two-carbon homologation sequence involving, inter alia, Wadsworth-Horner-Emmons and Yamaguchi lactonisation reactions in the closing stages of the synthesis. The impact of substituent stereochemistries and protecting groups on the RCM reaction leading to various ten-membered lactones is also described.

A chemoenzymatic synthesis of the 12-membered macrolide (-)-cladospolide A

The enantiomerically pure cis-1,2-dihydrocatechol 7, which is obtained by microbial oxidation of chlorobenzene, has been converted, via a sequence of reactions including ring-closing metathesis and Yamaguchi lactonisation steps, into the natural product (-)-cladospolide A (1).

Asymmetric synthesis of (-)-)2E,4R,5S,11R)-cladospolide A, induced by chiral sulfoxides

An enantioselective synthesis of (-)-cladospolide in which all the chiral centers are created by asymmetric reduction of β-ketosulfoxides, is reported.

Synthetic Microbial Chemistry, XV. - Synthesis of (2E,4R,5S,11R)-(-)-Cladospolide A, a Phytotoxic Macrolide from Cladosporium cladosporioides

The total synthesis of cladospolide A was achived in 16 steps from ethyl (R)-3-hydroxybutanoate (2a).

Synthesis of (4R,5S,11R)-(-)-Cladospolide A, a Phytotoxic Macrolide from Cladosporium cladosporosides

A total synthesis of cladospolide A was achieved in 16 steps from ethyl (R)-3-hydroxybutanoate.