87697-98-1Relevant academic research and scientific papers
Enantioselective total synthesis of (-)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step
De Brabander, Jef,Oppolzer, Wolfgang
, p. 9169 - 9202 (2007/10/03)
The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C4-C8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield.
Total synthesis of (-)-denticulatins A and B using efficient methods of acyclic stereocontrol
Paterson, Ian,Perkins, Michael V.
, p. 1811 - 1834 (2007/10/03)
The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C10 in 35 led to (-)-denticulatin A (1).
Asymmetric Synthesis of (-)-Denticulatins A and B via Group-Selective Aldolization of a Meso Dialdehyde with a Chiral N-Propionylsultam.
Oppolzer, Wolfgang,Brabander, Jef De,Walther, Eric,Bernardinelli, Gerald
, p. 4413 - 4416 (2007/10/02)
Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers.Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is conve
Studies in Polypropionate Synthesis: Stereoselective Synthesis of (-)-Denticulatins A and B.
Paterson, Ian,Perkins, Michael V.
, p. 801 - 804 (2007/10/02)
(-)-Denticulatin B (2) was prepared in 9 steps (20percent yield) with 70percent overall ds starting from the ethyl ketone (R)-8.Key steps are the novel boron-mediated aldol/reduction, 8 -> 12, the titanium aldol coupling, 6 + 5 -> 18, and the HF-pyridine cyclisation, 20 -> 2.Epimerisation at C10 in 20 led to (-)-denticulatin A (1).
Stereoselective Synthesis of Alcohols, XXXVIII. - Stereoselective Total Synthesis of the Denticulatins
Andersen, Marc W.,Hildebrandt, Bernhard,Dahmann, Georg,Hoffmann, Reinhard W.
, p. 2127 - 2139 (2007/10/02)
The total synthesis of the denticulatins 1 is described.Key feature is the efficient generation of the C-1-to-C-9 building block 37 by three consecutive stereoselective carbon-carbon bond-forming steps using chiral allylboronates.The C10-to-C-17 building block was obtained by kinetic Sharpless resolution of an allylic alcohol followed by an Ireland-Claisen rearrangement. Key Words: Marine natural products / Hemiketal formation, selective / Denticulatins
Total Synthesis of (-)-Denticulatins A and B: Marine Polypropionates from Siphonaria denticulata
Ziegler, Frederick E.,Becker, Michael R.
, p. 2800 - 2805 (2007/10/02)
A synthesis of the marine polypropionates (-)-denticulatin A (2a) and B (2b) is described.The targets, which are β-hydroxy ketones wherein the hydroxyl group is also a tertiary hemiketal, are sensitive to acid dehydration.An open chain form (26) of the de
