Structural and synthetic studies of the spore germination autoinhibitor, gloeosporone.

@article{Schreiber1988StructuralAS,
  title={Structural and synthetic studies of the spore germination autoinhibitor, gloeosporone.},
  author={Stuart L. Schreiber and Sarah E. Kelly and J. A. Jun. Porco and Tarek Sammakia and Edward Martin Suh},
  journal={Journal of the American Chemical Society},
  year={1988},
  volume={110 18},
  pages={
          6210-8
        }
}
Gloeosporone 1 is an autoinhibitor of spore germination that was recently isolated from conidia of Colletotrichum gloeosporioides. The structure initially proposed by Meyer et al. contained an unusual oxOcane ring system (la). A stereoselective synthesis of one of the two possible stereoisomeric forms of the oxocane structure that cast doubt on the structural proposal is described. Reinvestigation of the natural product resulted in the formulation of a structure that contains a 14-membered… 

Figures from this paper

Gloeosporone – A Macrolide Fungal Germination Self‐Inhibitor Total Synthesis and Activity
Starting with (S)- or (R)-4-Bromo-1,2-epoxybutane [commercially available or readily made from (S)- or (R)-malic acid], both enantiomers of the germination self-inhibitor gloeosporone were
Synthesis of (-)-gloeosporone, a fungal autoinhibitor of spore germination using a pi-allyltricarbonyliron lactone complex as a templating architecture for 1,7-diol construction.
The synthesis of the germination self-inhibitor (-)-Gloeosporone is reported. The embedded 1,7-diol motif in the product is constructed by an ironcarbonyl tether controlled Mukaiyama aldol reaction.
Total synthesis of (-)-salicylihalamide.
A concise total synthesis of the potent cytotoxic marine natural products salicylihalamide A and B (la, b) is reported. Key steps of our approach were the asymmetric hydrogenation reactions of
Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitor geldanamycin.
TLDR
19-membered ansa-lactams, simplified analogues of the naturally occurring Hsp90 molecular chaperone inhibitor geldanamycin, were obtained by concise routes, the key steps being the combination of a ring-closing metathesis to give a 17- Membered ring followed by Claisen rearrangement to effect ring expansion.
Synthesis of medium ring ethers. Part 3. Disproof of the proposed 2,8-disubstituted oxocane structure for gloeosporone. Synthesis of pseudo-gloeosporone
Synthesis of the cis- and trans-2,8-disubstituted oxocane derivatives 2 and 3(carrying the unusual γ,δ-diketohexanecarboxylic acid side chain) by ozonolysis of the alkynes 14 and 18(prepared
Synthesis of 12- to 16-Membered-Ring Lactones
TLDR
The objective of this chapter is to present an overview of the macrolactonization of seco-acids in the total synthesis of natural products but to present other new effective procedures for the ring closure of 12- to 16-membered ring lactones.
Secondary metabolites isolated from Colletotrichum species.
TLDR
Structural and biosynthetic studies of the metabolites isolated from various Colletotrichum species are reviewed and their role in the development of plant diseases is studied.
A simple, convenient and expeditious approach to cineol
ABSTRACT: A convenient two-step protocol prepa-ration of cineol (1-isopropyl-4-methyl-7-oxabicyclo-[2,2,1]heptane) from -terpineol (p-menth-1-en-8-ol)is reported. The phenylselenoetherification of
...
1
2
3
4
5
...