3442-58-8Relevant academic research and scientific papers
Highly stereoselective and efficient total synthesis of (+)-laurencin
Baek, Seungyoup,Jo, Hyunil,Kim, Hansoo,Kim, Hyoungsu,Kim, Sanghee,Kim, Deukjoon
, p. 75 - 77 (2007/10/03)
(Chemical Equation Presented) A highly stereoselective and efficient asymmetric total synthesis of (+)-laurencin (1) has been accomplished from the known oxazolidinone 5 in 15 steps. The route features an efficient internal alkylation to form oxocene 3 fr
Synthesis of (+)-laurencin via ring expansion of a C-glycoside derivative
Fujiwara, Kenshu,Yoshimoto, Saori,Takizawa, Ayumi,Souma, Shin-Ichiro,Mishima, Hirofumi,Murai, Akio,Kawai, Hidetoshi,Suzuki, Takanori
, p. 6819 - 6822 (2007/10/03)
Laurencin was efficiently synthesized from a C-glycoside derivative based on ring expansion of the oxane part of the starting compound into an eight-membered cyclic ether via a ring-cleavage/ring-closing olefin metathesis process, stereoselective introduc
Total synthesis of (+)-laurencin: an asymmetric alkylation-ring-closing metathesis approach to medium ring ethers.
Crimmins,Emmitte
, p. 2029 - 2032 (2008/02/11)
[formula: see text] The enantioselective total synthesis of (+)-laurencin 1 is achieved in 18 steps from (S)-(+)-4-benzyl-3-benzyloxyacetyl-2-oxazolidinone. The key steps in this synthesis are an asymmetric glycolate alkylation leading to acyl oxazolidinone 2 and a subsequent ring-closing olefin metathesis to construct the oxocene core of 1. The approach to medium ring ethers utilized in this synthesis provides a general and efficient route to the cyclic core of other marine natural products.
Synthesis of medium ring ethers. 5. The synthesis of (±)-laurencin
Burton, Jonathan W.,Clark, J. Stephen,Derrer, Sam,Stork, Thomas C.,Bendall, Justin G.,Holmes, Andrew B.
, p. 7483 - 7498 (2007/10/03)
The enantioselective synthesis of (+)-laurencin 1 has been achieved in 27 steps from (R)-malic acid 20. The key steps involved methylenation of the lactone 49 followed by intramolecular hydrosilation of the enol ether 14 (Scheme 11) and one carbon homologation of the diol 13 to give the key ethyl substituted cyclic ether 59 (Scheme 13). The lactone 49 was obtained by two efficient routes, namely a Claisen ring expansion (Scheme 3) followed by cl-hydroxylation (Scheme 6) and a Yamaguchi lactonization (Scheme 11). Elaboration of the (E)-pentenynyl side chain (Scheme 18) and introduction of bromine (Scheme 19) completed the synthesis of (+)-laurencin 1.
Total synthesis of (+)-laurencin. Use of acetal-vinyl sulfide cyclizations for forming highly functionalized eight-membered cyclic ethers
Bratz, Matthias,Bullock, William H.,Overman, Larry E.,Takemoto, Tadahiro
, p. 5958 - 5965 (2007/10/02)
The enantioselective total synthesis of (+)-laurencin (1) is accomplished in 24 steps from allyl alcohol. The synthesis features an acetal-vinyl sulfide cyclization that forms the oxocene ring and introduces, with complete control, the Δ4 unsat
Total synthesis of (+)-laurencin
Tsushima,Murai
, p. 4345 - 4348 (2007/10/02)
The first total synthesis of (+)-laurencin (1), which is the most representative marine natural product isolated from red algae, is described via intermediates 2-18. Key steps in the synthesis include a facile oxidative preparation of 2, an effective conversion of 9a to 11, and a SmI2-catalyzed elongation reaction of 15, providing 16a.
