Zhao, Hui; Gao, Kai; Ma, Haichen; Yip, Tsz Chun; Dai, Wei-Min published the artcile< Synthesis of the C19-C30 bis-THF fragment of iriomoteolide-13a via stepwise SN2 cyclization and intramolecular syn-oxypalladation>, Application In Synthesis of 627-27-0, the main research area is iriomoteolide fragment preparation; alkyne cyclization asym dihydroxylation.
The C19-C30 bis-THF fragment I [stereo = R or S] of the proposed structure of iriomoteolide-13a were synthesized. The ω-mesyloxy-substituted stereotetrad possessing three continuous hydroxy groups was generated by an anti-aldol reaction and asym. dihydroxylation was the key steps. Upon heating in pyridine, the stereotetrad underwent an SN2 cyclization to form the C19-C22 THF ring chemoselectively. The propargylic alc., after cleavage of the C28-OPMB ether, was reduced to the corresponding allylic alc. with spontaneous removal of the C23-OTBS protecting group. Finally, the ene triol was subjected to the Pd(II)-catalyzed intramol. syn-oxypalladation to give the C23-C26 THF ring. It was found that the C21-OH group, which might form a chelated Pd(II) complex along with the C23-OH group, was tolerated during the syn-oxypalladation process.
Organic Chemistry Frontiers published new progress about Cyclization, stereoselective. 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Application In Synthesis of 627-27-0.
Referemce:
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Alcohols – Chemistry LibreTexts