38996-01-9Relevant articles and documents
Double diastereoselection in intramolecular photocycloadditions: A radical rearrangement approach to the total synthesis of the spirovetivane phytoalexin (±)-lubiminol
Crimmins, Michael T.,Wang, Zhuo,McKerlie, Lynne A.
, p. 1747 - 1756 (1998)
The highly stereoselective total synthesis of the phytoalexin (±)-lubiminol (1) has been accomplished. The synthesis relies on three pivotal transformations: (1) a conjugate addition-cyclization reaction to prepare a highly functionalized 2-carbomethoxycyclopentenone as a photocycloaddition substrate, (2) a double diastereoselective intramolecular photocycloaddition for a stereoselective intramolecular photoaddition reaction which establishes the central quaternary spirocenter, and (3) the transformation of the photoadduct into the required spiro[5.4]decane through a radical fragmentation-rearrrangement reaction.
Rearrangement of cyclobutyl carbinyl radicals: Total synthesis of the spirovetivane phytoalexin (±)-lubiminol
Crimmins, Michael T.,Wang, Zhuo,McKerlie, Lynne A.
, p. 8703 - 8706 (1996)
The total synthesis of the phytoalexin (±)-lubiminol 1 has been accomplished. The synthesis relies on a conjugate addition-cyclization reaction to prepare a photosubstrate for a stereoselective intramolecular photoaddition reaction. The photoadduct is and formed into the required spiro [5.4] decane through a radical fragmentation-rearrangement reaction.
Gronowitz et al.
, p. 887,890 (1978)
Continuous Pd-Catalyzed Carbonylative Cyclization Using Iron Pentacarbonyl as a CO Source
Lopatka, Pavol,Markovi?, Martin,Koó?, Peter,Ley, Steven V.,Gracza, Tibor
, p. 14394 - 14406 (2019/11/11)
This work discloses a continuous flow carbonylation reaction using iron pentacarbonyl as source of CO. The described transformation using this surrogate was designed for use in commonly accessible flow equipment. Optimized conditions were applied to a sca
Scalable synthesis enabling multilevel bio-evaluations of natural products for discovery of lead compounds
Zhu, Lizhi,Ma, Wenjing,Zhang, Mengxun,Lee, Magnolia Muk-Lan,Wong, Wing-Yan,Chan, Brandon Dow,Yang, Qianqian,Wong, Wing-Tak,Tai, William Chi-Shing,Lee, Chi-Sing
, (2018/04/05)
Challenges in the development of anti-cancer chemotherapeutics continue to exist, particularly with respect to adverse effects and development of resistance, underlining the need for novel drugs with good safety profiles. Natural products have proven to be a fertile ground for exploitation, and development of anti-cancer drugs from structurally complex natural products holds promise. Unfortunately, this approach is often hindered by low isolation yields and limited information from preliminary cell-based assays. Here we report a concise and scalable synthesis of a series of low-Abundance Isodon diterpenoids (a large class of natural products with over 1000 members isolated from the herbs of genus Isodon, which are well-known folk medicines for the treatment of inflammation and cancer), including eriocalyxin B, neolaxiflorin L and xerophilusin I. These scalable syntheses enable multilevel bio-evaluation of the natural products, in which we identify neolaxiflorin L as a promising anti-cancer drug candidate.