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Graphical Abstract: Eur. J. Org. Chem. 15/2011
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201190038
Subject(s) - chemistry , intramolecular force , polyketide , stereochemistry , cyclohexene , diterpene , total synthesis , organic chemistry , catalysis , biosynthesis , enzyme
The cover picture shows a synthetic n ‐puzzle, a game that challenges players to move tiles along unbending routes in order to establish a certain end configuration. Our templated 1,3,9‐decatrienoate precursors, advanced synthetic tiles, were designed on the basis of a chiral 1,3‐dioxane tether and paved the way for stereodirected intramolecular Diels–Alder reactions, leading to asymmetric cyclohexene rings. The 1,3‐dioxane tether was expected to rigidify the decatrienoate system for efficient stereocontrol, with the ester carbonyl group strongly favoring endo ‐boat transitions states. Thanks to this method we succeeded in synthesizing valuable intermediates towards the total synthesis of the diterpene harringtonolide originating from the plum yew shown in the background and the fungal polyketide pyrrocidine A. Details of this work are described in the article by B. Nay et al. on p. 2789 ff.