Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C15H15OP, Application of (R)-Oxiran-2-ylmethanol.
White, James D. published the artcileStudies of the Synthesis of Providencin: Construction and Assembly of Two Major Subunits, Application of (R)-Oxiran-2-ylmethanol, the publication is Journal of Organic Chemistry (2014), 79(2), 700-710, database is CAplus and MEDLINE.
The “northern” sector of the cembranoid diterpene providencin (I) containing a tetrasubstituted cyclobutane was synthesized from the bis(acetonide) of D-glucose using dicyclopentadienylzirconium(0)-mediated oxygen abstraction from a furanose. Oxidative scission of the vinyl substituent of this cyclobutane gave an aldehyde, which was reacted with an alkynylstannane to provide an allenol (II). Cyclization of the derived allenone with silver nitrate led to a cyclobutylfuran (III) comprising the northern subunit of providencin. The “southern” sector of the cembranoid skeleton containing a trisubstituted iodoalkene attached to an α-phenylselenyl-γ-lactone was synthesized from (R)-glycidol. Negishi carbometalation-iodination established the (E)-iodoalkene, and addition of the lithio dianion of phenylselenoacetic acid to a tosylate generated the substituted lactone (IV). The two sectors were joined via stannylation of the furan of the northern component followed by Stille cross-coupling of the furylstannane with the iodoalkene of the southern subunit. Linkage of the two segments was also made at C12-C13 of providencin using intermol. aldol condensation of the enolate from the selenyl lactone of the southern portion with an acetaldehyde appendage on the cyclobutane of the northern sector. Closure of the providencin macrocycle from these conjoined subunits was unsuccessful.
Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C15H15OP, Application of (R)-Oxiran-2-ylmethanol.
Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts