Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390-3400): Но, R dibromide + PBr3 R ÕH 1 2 3 Modify the given structure to draw a structure for the desired product (2). Но OH Edit Drawing

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Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem201277, 3390–3400):

Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel
seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of
lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar
in function to PBr3 (J. Org. Chem. 2012, 77, 3390-3400):
HO
PBr3
R
dibromide +
R
ÕH
1
2
3
Modify the given structure to draw a structure for the desired product (2).
Но
OH
Edit Drawing
Transcribed Image Text:Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390-3400): HO PBr3 R dibromide + R ÕH 1 2 3 Modify the given structure to draw a structure for the desired product (2). Но OH Edit Drawing
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