Papers that relate to Step 1 (Wittig Olefination):

“Generation of phosphoranes derived from phosphites. A new class of phosphorus ylides leading to high E selectivity with semi-stabilizing groups in Wittig Olefinations” Aggarwal, V.K.; Fulton, J.R.; Sheldon, C.G.; De Vicente, J. J. Am. Chem. Soc. 2003, 125, 6034-6035.

The reaction in this article follows a Wittig-type process, creating a product that is highly E-selective.

“Total synthesis of (+)-phorboxazole A, a potent cytostatic agent from the sponge Phorbas sp.” Pattenden, G.; González, M.A.; Little, P.B.; Millan, D.S.; Plowright, A.T.; Tornos, J.A.; Ye, T. Organic and Biomolecular Chemistry 2003, 1, 4173-4208.

 This article discusses an alternate olefination reaction that produces an oxane-containing compound with multiple fused rings.

“Wittig-type olefination catalyzed by PEG-telluride” Huang, Z.-Z.; Ye, S.; Xia, W.; Yu, Y.-H.; Tang, Y. Journal of Organic Chemistry 2002, 67, 3096-3103.

 This article discusses Wittig olefinations because it studies a novel catalyst for Wittig-type reactions.

Papers that cited “Generation of Phosphoranes”

“Reactivity and selectivity in the Wittig reaction: A computational study” Robiette, R.; Richardson, J.; Aggarwal, V.K.; Harvey, J.N. J. Am. Chem. Soc. 2006, 128, 2394-2409.

The authors cited “Generation of Phosphoranes” to provide an example for Witteg Olefination.  The article studies the possibilities with this olefination, and “Generation of Phosphoranes” serves as an example.

“A practical, efficient, and atom economic alternative to the Wittig and Horner-Wadsworth-Emmons reactions for the synthesis of (E)-α,β- unsaturated esters from aldehydes” List, B.; Doehring, A.; Hechavarria Fonseca, M.T.; Job, A.; Rios Torres, R. Tetrahedron 2005, 62, 476-482.

The authors cited “Generation of Phosphoranes” to show a traditional example of Wittig Olefination and proceeds to offer an alternative to this traditional method.

“On the origin of high E selectivity in the Wittig reaction of stabilized ylides: Importance of dipole-dipole interactions” Robiette, R.; Richardson, J.; Aggarwal, V.K.; Harvey, J.N. J. Am. Chem. Soc. 2005, 127, 13468-13469.

“Generation of Phosphoranes Derived from Phosphites. A New Class of Phosphorus Ylides Leading to High ESelectivity with Semi-stabilizing Groups in Wittig Olefinations”

The reaction mechanism found in this paper is very similar to the mechanism of the Wittig Olefination found in the transformation of 69 to 70.  In this paper, the authors react hydrazones with aldehydes in order to form a carbon-carbon double bond in place of the C=N bond.  In this reaction, an SN₂ substitution takes place with (MeO)₃P being substituted for the two nitrogen molecules, releasing N₂.  A carbanion is formed on the carbon α to the (MeO)₃P, and this carbanion attacks the electrophilic carbon of the aldehyde, and via a cyclic intermediate, it forms primarily the final olefinated trans product.  This type of reaction mechanism is important to the understanding of the transformation of 69 to 70, in which an aldehyde is converted to an alkene by basically the same mechanism; the only difference is that 70 is the kinetic product that results from the cis ylide intermediate and therefore forms the E stereoisomer.