66261-30-1Relevant articles and documents
Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer
Yuan, Gucheng,Liu, Jiawei,Yu, Shihang,Wang, Xueyang,Bian, Qinghua,Wang, Min,Zhong, Jiangchun
supporting information, p. 80 - 83 (2021/10/05)
The synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans' chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.
Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**
Cunha, Ana V.,Havenith, Remco W. A.,Holzheimer, Mira,Minnaard, Adriaan J.,Schouten, Stefan,Sinninghe Damsté, Jaap S.
supporting information, p. 17504 - 17513 (2021/07/06)
Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66-membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.
A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth
Bai, Hongjin,Du, Zhen-Ting,He, Guo-Guo,Liu, Lu,Tang, Meng,Wei, Liang,Zhang, Tao
, p. 1089 - 1095 (2020/07/25)
Abstract: An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of thepeach leafminer moth has been achieved. Based on the asymmetric methylation ofchiral (S)-4-benzyloxazolidin-2-one, thecarbon chain of the target molecule was assembled through aC1+C10+C4+C3procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid andthen, with the induction of Evan’s template, a chiral methyl group wasintroduced to the position of the carboxylic group in 97percent de. After reduction and a couple of chemicaloperations, the designed key intermediate A1was obtained. The synthesis of another moiety was started from decane-1,10-diolwhich was selectively protected and oxidized. The long carbon chain wasinstalled according to a Wittig protocol. After deprotection, oxidization, andmethylenation, the target molecule was synthesized in 7 linear steps with anoverall yield of 30.3percent.
Synthesis, Profiling, and Bioactive Conformation of trans-Cyclopropyl Epothilones
Kuzniewski, Christian N.,Glauser, Simon,Gaugaz, Fabienne Z.,Schiess, Raphael,Rodríguez-Salarichs, Javier,Vetterli, Stefan,Horlacher, Oliver P.,Gertsch, Jürg,Redondo-Horcajo, Mariano,Canales, Angeles,Jiménez-Barbero, Jesús,Díaz, José Fernando,Altmann, Karl-Heinz
, (2019/05/10)
A series of new 3-deoxy-C(12),C(13)-trans-cyclopropyl-epothilones have been prepared, bearing benzothiazole, quinoline, thiazol-5-ylvinyl, or isoxazol-3-ylvinyl side chains. For analogs with fused aromatic side chains, macrocyclic ring-closure was based on ring-closing olefin metathesis (RCM) of a precursor incorporating the fully elaborated heavy atom framework of the target structure (including the side chain moiety), while side chain attachment for the thiazole and isoxazole-containing 16-desmethyl analogs was performed only after establishment of the macrolactone core. Two approaches were elaborated for a macrocyclic aldehyde as the common precursor for the latter analogs that involved ring-closure either by RCM or by macrolactonization. Benzothiazole- and quinoline-based analogs were found to be highly potent antiproliferative agents; the two analogs with a thiazol-5-ylvinyl or an isoxazol-3-ylvinyl side chain likewise showed good antiproliferative activity but were significantly less potent than the parent epothilone A. Surprisingly, the desaturation of the C(10)?C(11) bond in these analogs was associated with a virtually complete loss in antiproliferative activity, which likely reflects a requirement for a ca. 60 ° C(10)?C(11) torsion angle in the tubulin-bound conformation of 12,13-trans-epothilones.
Toblerols: Cyclopropanol-Containing Polyketide Modulators of Antibiosis in Methylobacteria
Ueoka, Reiko,Bortfeld-Miller, Miriam,Morinaka, Brandon I.,Vorholt, Julia A.,Piel, J?rn
supporting information, p. 977 - 981 (2017/12/26)
Trans-AT polyketide synthases (PKSs) are a family of biosynthetically versatile modular type I PKSs that generate bioactive polyketides of impressive structural diversity. In this study, we detected, in the genome of several bacteria a cryptic, architectu
Stereoselective synthesis of the Paulownia bagworm sex pheromone
Sun, Zhi-Feng,Zhou, Lu-Nan,Zhang, Tao,Du, Zhen-Ting
, p. 558 - 562 (2017/06/19)
According to our retrosynthesis, the main chain of the target molecule could be constructed using a C5?+?C7?+?C5 strategy. The key induction reaction afforded chiral methyl group moieties using different Evans templates with different configurations. Li2CuCl4 was effectively employed in the Csp3[sbnd]Csp3 coupling protocol. The target molecular was obtained in a 12.6% overall yield with nine steps in the longest linear route.
Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones - Tools and tactics for solving problems in fluorous mixture synthesis
Dandapani, Sivaraman,Jeske, Mario,Curran, Dennis P.
, p. 9447 - 9462 (2007/10/03)
The application of fluorous mixture synthesis (FMS) for accessing natural products and their stereoisomers was validated by the total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone. Four fluorous p-methoxybenzyl groups were used as tag
Synthetic studies toward potent cytotoxic agents amphidinolides G and H: Synthesis of the entire C15-C26 moiety of the top half
Chakraborty,Suresh
, p. 7775 - 7778 (2007/10/03)
Stereoselective synthesis of the entire (16S, 18S, 21R, 22S, 23R, 25R)- C15-C26 segment 1 of amphidinolides G and H has been achieved for the first time following a highly efficient convergent strategy.
Total synthesis of archaeal 36-membered macrocyclic diether lipid
Eguchi, Tadashi,Arakawa, Kenji,Terachi, Takumi,Kakinuma, Katsumi
, p. 1924 - 1933 (2007/10/03)
Total synthesis of archaeal 36-membered macrocyclic diether lipid 2 is reported. The synthesis is based upon stereoselective preparation of functionalized isoprenoid chains, ether-linkage formation between the isoprenoid chains with a glycerol derivative,
The First Synthesis of an Archaebacterial 36-Membered Macrocyclic Diether Lipid
Eguchi, Tadashi,Terachi, Takumi,Kakinuma, Katsumi
, p. 137 - 138 (2007/10/02)
The archaebacterial macrocyclic diether lipid featuring of 36-membered ring is synthesized by the McMurry coupling as a key step.
