VjCD0100ChemDraw 9.0Problem_Templ.cdx# q y7 f f jv :;<   `  xx# $$$$qq ccUU qq"" OO ' HelveticaxL4g(HH(d}h R$$s ih ft ih fxKF TS  >89 7>  $0h  5G   TS` 7N Np 7P DO ] \?ٲ  7S\?OOJ iL6  +O#5cH#O# `OK \?O N mG2m   O N J L J K CCrܨ;rvBC f#`OMe_ Lj#  7TLj#;vQ Lj# R Lj5  S R Q 'û*^'û#`Mea Lj#\" 7ULj#\;(IU Lj#\" V Lj5\"  W V U '^'#`Mec dMe 7VUvIf=Y `cbϳ +fh,^hIfh `OZ Uv \ ]  ] \ Y ^ Y Z jhfs~ahfs#`OMee 53 7W53gN` 53 a G3  b a ` I9L[19L#`Meg 5>g 7i Xin 7XXiTZp5d Xin e jin  f e d K\|ӎT颯'r\|#`Meq 5G s 5Y +7\[]U[][â# `Ov 5>S 7| 5Gx ~ 5>%p !7 5Yx #7Y5Yxy]\qDh 5Yx i 5kx  j i h \v{+Uv{*]O#`Me 5G-` %7 5>P ' 5,P )7 5#aA * 5,>1 +7 5>>1 , 5GaA - 5aA 47Z]|3\$Xl 6-I +hFE]FEM `Om X n 9  o n l p l m |{= |{=S#`OMe 5YaA 67[]H#\Z6-Ir K9 +hO*5]H*5O*p= `Os T6-I t T)  u t r v r s \|{=]U|{=]S#`OMe 5G4" 87\5G]\_e[(x 5G4" y 5Y4"  z y x JB&+Ci*KB&#`Me                    O N  d Y Q  P  Y ^ Y  P N ^  P ] `  _ b  a d c f e h  g j  i r g q u q s x q v }  v |  "| ~   }  $|   &~   (   .     /   0     1   2     3   5   7   9   p9J7uy dY ;01  dY <01  dQi = d7x >7 d7x ?7 dQi @7 dQi G+7+keQ+keJ++m# `O dG I7 dG J $qt\Y N7]J^\Gd\kdv\Y d01dv\k ed\Y fdv\G gdd\Y h  i j k lW$x(BVp(BVzxo#`CMe3 ӭY P+7(V (Vȱ[]# `H ; R7 A   B   C   D   E   F   H   K   L   M   O    Q    S   <P2 P T7^zb;oϸ d< +uQuX<# `B }< +iziDoϸ#`Cl )< +\iGioϸ#`Cl d< +ȡQb;Jȡ#`Cl         d<<P2#`BCl3 p!3 pԛ. ^ /^`! _ -` a7 SFj b q  d  zi g7 /e i [2 l7 .`K( n7 s q7_sKߋ sK U K V  W  xw1p4w1#`Me st s7`sMߋɎ sg X g Y  Z  xwc.pc.w##`Me , u+7_ƸT_TT # `O S w7aFԬm F [ F \  ]  \!G#`Me ^Q y7 `   c    e    f   h   j   k   m   o   p   r   t   v   x   z   vns@ ٹe }017 # / (  ڹe ~019 # $ 2  ڹ<  ڹⒽ 7 ٹⒽ 7! ٹ< 7) )G 01; / 0 = + ڹ 7- IG 6 ٹwe 7bٹwKc ٹwe  ٹe      m{0t0{#`Me8 ڹe +7 mŚŚ# `H: )rG 7c)r-Pm)rG )G   uvnvRږ#`Me< ){z} 7d){zwPF׃){z} )z}   ~vws#`Me> ڹ< +7 m@ձ# `OA Eh, 7#   $   %   &   '  ! ( !  /  ) 0 ) + 1 + - 2 -  7  6  9  8  ; ) :  = ) <  @  > C - A  :XZ dZ 01  d$Z 01  d-Qj  d$7y 7 d7y 7 d Qj 7 d?Qj +!7CRmQ;^JCRm#`OH dH 7 d$H  ٹZ 7eJHdldZ m01dl ndZ odH pdZ q  r s t u m[5W[5W?kp#`CMe3 ~6Z +71:(W2(Ws:[^# `H 1< 7 L w 7f8Kh_ߎ/L w +!OsFsP؃#`BH-0[ n +h_vqOXKh_vq#`Cl17< n +j;@vq8Khn@vq#`Cl2L +OxkHxBPߎ#`Cl3 /04 /15 /2OskHsCER#`BHCl3                                                 Eka EkW  !   /T-]p/T-]f  !   pn>QE iT 7 iT  S$Qa 7 S$Qs  iC 7 iC 7 Qs 7 Qa ! Q5z 7gJ*R܌mg v+ YccSk `Orw w+!YssY }#`B-| x+|J|DRO#`Cl y+0Yuuc܌#`Cl(+|n z+[!rwEh!r#`ClDX {  | } ~  xNv\NvQE#`OBCl3 aMTC 7 dnZ  vce 7hvI_kzk]vce ^ƈce  _ ^]yzGaksGa׺zn#`Me H 7i{BۚNaH bH  c ba hLn>&L#`Me 'mtS 7j'mtqMYe'mtS f'mS  g feZ x3WpI`ax3W#`Me                                             1e1[  !  fD6#D6# I !   zy9QE; i 7 i  S$Q  7 S$Q iC ) 7iC ) 7Q 7Q  aMT 7Q5# 7kJ*5m + Y  S `Or  +!YY &#`B-|) +%J%DRO/#`Cl0 +0Yu,u,c5#`Cl(+| +[!wE!#`ClD       xN\NQE;#`OBCl3Q  ! 7l-v w  x wv0Bm##`Me 7mm֙[ z {  | {zb(m}(٣{##`MeD 7nDm֙~D D   ~b]m}٣]#`Me                                          _S _S  !  gS*S* J!  jPUPgikPg 7kkPU 7l ik uPk I (* -" ( 7 ' 7xȺ 7"*ӑ  dR0*ӑ  7o>|j    +7,b&J b&_b# `Ow[r 7ow[X`'?w[r Aw[r  B A?*+`+k#`Me"~ _9 7p~ _K%+`~ _9 ~_9   <xGK m|}xG#`Me$%-z 7q%-`yb=%-z 7-z   m)Fb"uή)F#`Me&kOœ 7-F} +7F݀aF݀y# `Hqhk' v7rv|CFqhk' +!\#`B-Gj' +̻f1̻#`ClHph +*=*NC#`ClIk' +I7K7|#`ClMqh Ɛ  N MFO FGJ FHK FI>׎k#`BCl3   .                   .        # " % $ .( &. - % w +^ 2r^  !  kk'kk' x!  \ <8yO9 $7O5  %m4u &7!Ω y '01 WAb (7 m4u -2This atom is very close to another atom or bond. !Ω y /7 # 17z 4/An atom in this label has an invalid valence.7sWoC  +پ|sX| | `ODMQ +#yG#y# `BE 1E +ھtXW #`ClF1E +'JWZ}#`ClG +'J&&Z}#`ClMn@  N MCH CDI DEJ DFK DGG-gƦgz#`OBCl3!Η y 67t!Η _؟P!Η y Q!Ω y  R QPT2fē2? #`Me)z y 8ۊ :7u\Tۊ Uۊ  V UTo\ ?Ȱ#`Me2 <7v2|Y*X2 Y2  Z YX);)<8y #`MeO5  >7 )  *  +  ,   .    0   2     3    5   7  9  ;  =   ?! NLJz̃ @!  \.Aua=]ax H7w]Ff$ڌ_~ A+ZzbzΛ'# `B` B+"Kt]KtUڌ#`Cla:> C+mKtKt$ڌ#`Clbl D+Z obFf o#`Clc E_`d F_ae G_bu.Aua=#`BCl3hC$^d&SSS;i) TjU0a UkS W7lI XmD t  Zn1$} ]7oU0ѻ _p8,^0 b7qT!N% d7rV g7xN/ptNI KuNI L v Mut4dC$4d#`Mew i7yy Nz O { PzyfCf$^ #`Me|RDB  k/An atom in this label has an invalid valence.+7EW'>W'*FW# `O}) m7zw+Cw Qw% R  S77$^x7#`Me&Ba o7LS* r/An atom in this label has an invalid valence.7{&9L }`a?Ld) +1P&LI&7Pd,# `B\d  +I`I$qX }`I$#`ClC  +1GJL@LdGJ#`ClYi=d2 +A0/&90/OAw8#`ClU ;9      1P'LI'd&SSS;#`BCl3 Vij  Ykl  [im  \lm  ^ln  `no  aio  cjp  ekq  fqp  hmr  jmw  lj|  nl}  po s| ;r # q ?{ &ChemDraw cant interpret this label. 8s VcdhThe synthesis of racemic tetramethylmediterraneol B was reported by workers in Japan (J. Org. Chem. 1995, 60, 3318-33). The pivotal step was the rearrangement of compound 1 into the [4.2.1] bicycle 2, as found in the natural product. Provide a mechanism for the formation of 2 and 3.  ϩh ȨhI :&ChemDraw cant interpret this label.&tetramethylmediterraneol B c?u8?- |&ChemDraw cant interpret this label."2, 66% yieldD c?u8? &ChemDraw cant interpret this label."3, 11% yieldE ڹ=RsS6Rs X 5This label has conflicting or unassignable charges. +F dQZtPZ(^_ &ChemDraw cant interpret this label. 1 iQQ &ChemDraw cant interpret this label.[1,2] Me shiftli$a$f* #&ChemDraw cant interpret this label. '3Ring expansion to 9-membered carbacycleW2 1i3 1>( {&ChemDraw cant interpret this label. eN[\ Dear Contributor: This ChemDraw template should be used for any questions that you wish to submit. Mail your question/answer along to me as a single ChemDraw file. When the question is entered into the database, your authorship will be duly noted noted as part of the question. Please note the color scheme for curved arrows and commentary. The purpose of this website is to share problems with the scientific community. Your willingness to participate is deeply appreciated. Dave Evans: evans@chemistry.harvard.eduPԘ`n2Y;?b7 }&ChemDraw cant interpret this label.Answer: d=d= {     b'cH$͒Y     ! | d?Qrd7Qj     ! | s[[i[[     !  iQiQ    #a_!     ! |$iQiQ     ! {_%n{_%n    l -PJ -P     ' 1'  !   kVХkХ "   KG( ih(  q    W W t   w3; u    ! PLb<* y    ! Lb.Y z    ! XX1Wg |   |}      \~                 j   j  h  j    h