14947-48-9Relevant academic research and scientific papers
N-heterocyclic carbene catalyzed oxidative macrolactonization: Total synthesis of (+)-dactylolide
Lee, Kiyoun,Kim, Hyoungsu,Hong, Jiyong
supporting information; experimental part, p. 5735 - 5738 (2012/08/14)
Three key steps constitute the total synthesis of (+)-dactylolide: the 1,6-oxa conjugate addition reaction of a 2,4-dienal for the facile synthesis of the 2,6-cis-2-(4-oxo-2-butenyl)tetrahydropyran subunit, the umpolung alkylation reaction of a cyanohydrin, and the NHC-catalyzed oxidative macrolactonization reaction for the synthesis of the 20-membered macrocyle. NHC=N-heterocyclic carbene. Copyright
Intramolecular methylation of an allyl sulfone via lithium alkoxyaluminate; Application to the enantioselective synthesis of the CD ring of vitamin D 3
Sikervar, Vikas,Fuchs, Philip L.
supporting information; experimental part, p. 2922 - 2924 (2012/07/28)
Alcohol-directed intramolecular methylation of an enantiopure allyl sulfone using AlMe3 provides a trans-hydrindane CD ring alcohol. The substrate cis-CD ring allyl sulfone alcohol is prepared via intramolecular allyl sulfonyl anion addition to aldehyde using Ba(OH)2.
Enantioselective synthesis of structurally intricate and complementary polyoxygenated building blocks of spongistatin 1 (altohyrtin a)
Braun, Alain,Cho, Ii Hwan,Ciblat, Stephane,Clyne, Dean,Forgione, Pat,Hart, Amy C.,Huang, Guoxiang,Kim, Jungchul,Modolo, Isabelle,Paquette, Leo A.,Peng, Xiaowen,Pichlmair, Stefan,Stewart, Catherine A.,Wang, Jizhou,Zuev, Dmitry
experimental part, p. 651 - 769 (2010/02/27)
Enantioselective approaches to the construction of four complex building blocks of the structurally intricate marine macrolide known as spongistatin 1 are presented. The first phase of the synthetic effort relies on a practical approach to a desymmetrized, enantiomerically pure spiroketal ring system incorporating rings A and B. Concurrently, the C17-C28 subunit, which houses one-fifth of the stereogenic centers of the target in the form of rings C and D, was assembled via a composite of stereocontrolled aldol condensations. Once arrival at the entire C1-C28 sector had been realized, routes were devised to provide two additional highly functionalized sectors consisting of C29-C44 and C38-C51. A series of subsequent transformations including cyclization of the E ring and hydroboration to afford the B-alkyl intermediate for the key Suzuki coupling to append the side chain took advantage of efficient stereocontrol. Ultimately, complete assembly and functionalization of the western EF sector of spongistatin was thwarted by an inoperative Suzuki coupling step intended to join the side chain to the C29-C44 sector, and later because of complications due to protecting groups, which precluded the complete elaboration of the late stage C29-C51 intermediate.
Synthesis of the C-1-C-28 ABCD Unit of Spongistatin 1
Gaunt, Matthew J.,Jessiman, Alan S.,Orsini, Paolo,Tanner, Huw R.,Hook, David F.,Ley, Steven V.
, p. 4819 - 4822 (2007/10/03)
(Equation Presented) The synthesis of the C-1-C-28 ABCD fragment of spongistatin is described. Anti-selective boron-mediated aldol coupling of a CD spiroketal ketone fragment to an AB spiroketal aldehyde unit forms the desired C1-C28 advanced intermediate
A Practical and Efficient Synthesis of the C-16-C-28 Spiroketal Fragment (CD) of the Spongistatins
Gaunt, Matthew J.,Hook, David F.,Tanner, Huw R.,Ley, Steven V.
, p. 4815 - 4818 (2007/10/03)
(Equation Presented) A practical and efficient route to the CD spiroketal (C-16-C-28) of the spongistatins is reported. Two stereocenters are introduced from chiral building blocks with the remainder introduced by substrate-controlled transformations. The
Stereochemical elucidation of the 1,4 polyketide amphidinoketide I.
Walsh, Louise M,Goodman, Jonathan M
, p. 2616 - 2617 (2007/10/03)
The relative and absolute stereochemistry of amphidinoketide I has been determined by the total synthesis of all the diastereoisomers. Molecular modelling suggests that the natural product is not the thermodynamically preferred diastereoisomer.
A CONDENSED SYNTHESIS OF DIHYDRO-3(2H)-FURANONE
Tarnchompoo, Bonkoch,Thebtaranonth, Yodhathai
, p. 5567 - 5570 (2007/10/02)
A straight forward synthesis of dihydro-3(2H)-furanone is described.An attempted preparation of the oxetan-3-one precursor 10 by this method gave, instead, the ring enlargement product 11.
